Publications by authors named "Wen-Yong Han"

20 Publications

  • Page 1 of 1

Palladium-catalyzed asymmetric allylic alkylation of 3-aminooxindoles to access chiral homoallylic aminooxindoles.

Org Biomol Chem 2021 Jun;19(21):4720-4725

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563000, China. and Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563000, China.

An organometal catalytic conversion of 3-aminooxindoles for the diastereo- and enantioselective synthesis of homoallylic aminooxindoles has been described. The asymmetric allylic alkylation of 3-aminooxindoles with allyl carboxylates proceeded smoothly to afford a series of chiral 3-allyl-3-aminooxindoles. This work offers an alternative route to build these scaffolds. The application of this protocol is also highlighted by a significant conversion of products to the potential applicable spiro[indoline-3,2'-pyrrolidin]-2-one derivatives.
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http://dx.doi.org/10.1039/d1ob00550bDOI Listing
June 2021

Synthesis of chromone-containing polycyclic compounds via palladium-catalyzed [2 + 2 + 1] annulation.

Org Biomol Chem 2020 02 27;18(6):1112-1116. Epub 2020 Jan 27.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563006, P. R. China. and Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563006, P. R. China.

A palladium-catalyzed [2 + 2 + 1] domino annulation of 3-iodochromones, α-bromo carbonyl compounds, and tetracyclododecene (TCD) is described. This approach provides a facile, efficient and atom-economical route to a variety of chromone-containing polycyclic compounds bearing fused/bridged-ring systems in good yields (up to 81%) with excellent diastereoselectivities (99 : 1 dr in all cases).
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http://dx.doi.org/10.1039/c9ob02690hDOI Listing
February 2020

Generation of Difluorodiazoethane (CFHCHN): Application in the Regioselective Synthesis of CFH-Containing Pyrazoles.

Org Lett 2019 11 23;21(21):8751-8755. Epub 2019 Oct 23.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy , Zunyi Medical University , Zunyi 563006 , P. R. China.

A new method for the generation of difluorodiazoethane (CFHCHN) and a procedure for its efficient use in [3 + 2] cycloaddition with nitroolefins by the AcOH/O catalyst system were developed by using a simple two-chamber system. The method provides a facile and straightforward access to a series of 4-substituted 5-difluoromethyl-3-nitro-1-pyrazoles that are of interest in medicinal chemistry. Interestingly, the key factor for the success of this method is the efficient preparation of CFHCHN by an process.
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http://dx.doi.org/10.1021/acs.orglett.9b03371DOI Listing
November 2019

2,2-Bifunctionalization of Norbornene in Palladium-Catalyzed Domino Annulation.

Org Lett 2019 11 22;21(21):8857-8860. Epub 2019 Oct 22.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy , Zunyi Medical University , Zunyi 563006 , PR China.

A palladium-catalyzed three-component [2 + 3 + 1] domino annulation among 3-iodochromones, α-bromoacetophenones, and norbornene is presented, affording various chromone-containing polycyclic compounds bearing fused/spiro/bridged-ring systems. For the first time, the 2,2-bifunctionalization of norbornene was realized in palladium-catalyzed domino reaction. This cyclization characterizes three new bonds (two C-C and one C-O) in a single operation and produces nontrivial spiro-norbornane fragments in comparison with a traditional palladium-catalyzed process involving norbornene.
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http://dx.doi.org/10.1021/acs.orglett.9b03565DOI Listing
November 2019

Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3'-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters.

J Org Chem 2018 09 11;83(17):10465-10475. Epub 2018 Jul 11.

Generic Drug Research Center of Guizhou Province, School of Pharmacy , Zunyi Medial University , Zunyi 563000 , China.

A highly regio- and stereoselective [3 + 2] cycloaddition reaction for constructing novel 3,3'-cyclopentenyldispirooxindoles incorporating two adjacent quaternary spirostereocenters is reported. Under the mild conditions, the asymmetric annulation of isatin-derived MBH carbonates with 3-methyleneoxindoles involving a chiral tertiary amine catalyst provides the corresponding dispirooxindole frameworks with an extraordinary level of enantioselective control. Further synthetic utility of this method was demonstrated by the gram-scale experiment and simple transformation of the obtained product. Moreover, a plausible mechanism for this annulation reaction was also proposed on the basis of the control experiments.
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http://dx.doi.org/10.1021/acs.joc.8b01506DOI Listing
September 2018

A Protocol for the Synthesis of CFH-Containing Pyrazolo[1,5- c]quinazolines from 3-Ylideneoxindoles and in Situ Generated CFHCHN.

J Org Chem 2018 06 4;83(12):6556-6565. Epub 2018 Jun 4.

Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy , Zunyi Medical University , Zunyi 563000 , China.

Herein is disclosed a selective and facile approach for the construction of CFH-containing pyrazolo[1,5- c]quinazolines from easily accessible 3-ylideneoxindoles and in situ generated CFHCHN. The reaction involving a [3 + 2] cycloaddition/1,3-H shift/rearrangement/dehydrogenation cascade proceeded smoothly at room temperature in the absence of catalyst and additive. Moreover, this metal-free process along with mild conditions is desirable and valuable for the pharmaceutical industry. Importantly, this reaction features a broad substrate scope, good functional group tolerance, and gram-scale synthesis.
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http://dx.doi.org/10.1021/acs.joc.8b00866DOI Listing
June 2018

Diastereoselective [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CFHCHN: syntheses of CFH-containing spirooxindoles.

Org Biomol Chem 2017 Jul;15(26):5571-5578

Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, 563000, China.

An efficient [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CFHCHN for the syntheses of spirooxindoles has been developed. This methodology gives access to a range of relatively complex spirooxindoles featuring a CFH group and three contiguous stereogenic centers in up to 84% yield and 99 : 1 trans/cis.
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http://dx.doi.org/10.1039/c7ob01266gDOI Listing
July 2017

[Anesthesia and perioperative management for cesarean section in patient with factor XI deficiency: a case report].

Beijing Da Xue Xue Bao Yi Xue Ban 2014 Apr;46(2):329-32

Department of Anesthesiology, Peking University Third Hospital, Beijing 100191, China.

Factor XI deficiency is a hereditary blood coagulation disorders. Puerpera with factor XI deficiency is exceedingly rare. A case of a 28-year-old woman who was found to have factor XI deficiency coagulopathy at the end of 33 weeks of gestation was presented here, and was admitted to Peking University Third Hospital at the end of 38 weeks of gestation. The doctors from several departments conducted cooperative management, and prepared with supplement of the coagulant factor and fresh frozen plasma before operation. The woman had general anesthesia, the baby was delivered successfully and the mother's condition was kept stable. The amount of bleeding of puerpera was not much perioperation. Yet the management of cesarean section with factor XI deficiency at home and abroad is still lack of standard guideline by now.
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April 2014

Asymmetric synthesis of β-hydroxy-α-amino phosphonic acid derivatives via organocatalytic direct aldol reaction of α-isothiocyanato phosphonates with aldehydes.

J Org Chem 2013 Oct 2;78(20):10541-7. Epub 2013 Oct 2.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.

α-Isothiocyanato phosphonates are first used as nucleophiles to react with aldehydes for the asymmetric synthesis of β-hydroxy-α-amino phosphonic acid derivatives. The process is catalyzed by a quinine-derived thiourea via cascade aldol/cyclization reaction, affording a wide range of protected β-hydroxy-α-amino phosphonates containing adjacent quaternary-tertiary stereocenters in up to 93% yield, up to 81% ee, and >99:1 dr. This work represents the first example of α-isothiocyanato phosphonates serving as nucleophiles that are used in the catalytic asymmetric synthesis.
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http://dx.doi.org/10.1021/jo401779xDOI Listing
October 2013

Enantioselective synthesis of quaternary 3-aminooxindoles via organocatalytic asymmetric Michael addition of 3-monosubstituted 3-aminooxindoles to nitroolefins.

J Org Chem 2013 Sep 21;78(17):8833-9. Epub 2013 Aug 21.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

An enantioselective synthesis of quaternary 3-aminooxindoles with 3-monosubstituted 3-aminooxindoles as nucleophiles is first presented. A Michael addition reaction of 3-monosubstituted 3-aminooxindoles to nitroolefins has been developed with a bifunctional thiourea-tertiary amine as a catalyst to afford a range of 3,3-disubstituted oxindoles bearing adjacent quaternary-tertiary centers in good results (up to 98% yield, >99:1 dr, and 92% ee). We also demonstrate the potential synthetic utility of this methodology by a transformation of the product into a spirocyclic oxindole compound.
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http://dx.doi.org/10.1021/jo401154bDOI Listing
September 2013

3-isothiocyanato oxindoles serving as powerful and versatile precursors to structurally diverse dispirocyclic thiopyrrolidineoxindoles through a cascade Michael/cyclization process with amino-thiocarbamate catalysts.

Chemistry 2013 Apr 12;19(18):5551-6. Epub 2013 Mar 12.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, P R China.

Cascading catalysis: 3-Isothiocyanato oxindoles act as powerful and versatile precursors for a range of structurally diverse dispirocyclic thiopyrrolidineoxindoles containing two spiro-quaternary and three contiguous stereogenic centers in quantitative yields with excellent disatereo- and enantioselectivities by only using 1 mol % amino-thiocarbamate catalyst.
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http://dx.doi.org/10.1002/chem.201300206DOI Listing
April 2013

Highly efficient and stereocontrolled construction of 3,3'-pyrrolidonyl spirooxindoles via organocatalytic domino Michael/cyclization reaction.

Org Lett 2013 Mar 1;15(6):1246-9. Epub 2013 Mar 1.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

A wide range of structurally diverse 3,3'-thiopyrrolidonyl spirooxindoles bearing three contiguous stereogenic centers can be smoothly obtained via a domino Michael/cyclization reaction between 3-isothiocyanato oxindoles and 3-methyl-4-nitro-5-alkenyl-isoxazoles with commercially available quinine as the catalyst under mild conditions. The protocol is significantly characterized by high reactivity, a low catalyst loading (1 mol %), and an excellent diastereo- and enantioselectivity (up to >99:1 dr and 98% ee).
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http://dx.doi.org/10.1021/ol400183kDOI Listing
March 2013

FeCl3-catalyzed stereoselective construction of spirooxindole tetrahydroquinolines via tandem 1,5-hydride transfer/ring closure.

Org Lett 2012 Aug 3;14(16):4054-7. Epub 2012 Aug 3.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

An efficient FeCl(3)-catalyzed stereoselective intramolecular tandem 1,5-hydride transfer/ring closure reaction was developed. The method allows for the formation of structurally diverse spirooxindole tetrahydroquinolines in high yields (up to 98%) with good to excellent levels of diastereoselectivity (up to 99:1 dr). The catalytic enantioselective variant of this process was also investigated preliminarily with a chiral BINOL-derived phosphoric acid.
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http://dx.doi.org/10.1021/ol301559kDOI Listing
August 2012

Organocatalytic enantioselective stereoablative hydroxylation of 3-halooxindoles: an effective method for the construction of enantioenriched 3-substituted 3-hydroxy-2-oxindoles.

Chemistry 2012 Jul 19;18(29):8916-20. Epub 2012 Jun 19.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, PR China.

3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).
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http://dx.doi.org/10.1002/chem.201201395DOI Listing
July 2012

Enantioselective organocatalytic three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids.

Org Lett 2012 Feb 31;14(4):976-9. Epub 2012 Jan 31.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids with a newly designed thiourea-binol catalyst is presented. A broad range of alkylaminophenols can be obtained in good yield (up to 92%) and good to high enantioselectivity (up to 95% ee). A possible reaction pathway for this catalytic enantioselective Petasis reaction is tentatively proposed.
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http://dx.doi.org/10.1021/ol203109aDOI Listing
February 2012

Highly efficient and stereoselective construction of dispiro-[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles.

Org Lett 2012 Jan 11;14(2):490-3. Epub 2012 Jan 11.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

An efficient and stereoselective reaction between 3-isothiocyanato oxindoles and isatins/isatinimines has been developed to afford structurally diverse dispiro[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles in excellent results under mild conditions. The potential of asymmetric induction by means of a chiral auxiliary was explored. The isomers are separable, and products could be isolated as single diastereomers by column chromatography. Further synthetic transformations of the reaction product were also successfully realized.
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http://dx.doi.org/10.1021/ol203081xDOI Listing
January 2012

[A case of anesthesia for caesarean section in a late pregnant woman with recurrent femoral osteosarcoma].

Beijing Da Xue Xue Bao Yi Xue Ban 2011 Dec;43(6):908-10

Department of anesthesiology, Peking University Third Hospital, Beijing 100191, China.

Osteosarcoma is the most common malignant tumor primarily originated from bone, yet puerpera with osteosarcoma is exceedingly rare. We present here a case of a 27-year-old woman who was operated for femoral osteosarcoma 2 years ago. With emergency admission to Peking University Third Hospital she was diagnosed with recurrent osteosarcoma during the second trimester of pregnancy. As pregnancy might promote tumor development, the general principle demanded timely termination of pregnancy after diagnosis, but the patient insisted on giving up all her comprehensive cancer treatment. As a result, a well made plan for the protection of mother and child was carries out to perform cesarean delivery at the end of 32 weeks of gestation under general anesthesia. The baby was delivered successfully and the mother's condition was kept stable. This case highlighted the benefits of multidisciplinary cooperation and balanced the needs of the developing fetus with those of the mother.
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December 2011

Use of ultrasound to facilitate femoral nerve block with stimulating catheter.

Chin Med J (Engl) 2011 Feb;124(4):519-24

Department of Anesthesiology, Peking University Third Hospital, Beijing, China.

Background: The adjunction of ultrasound to nerve stimulation has been proven to improve single-injection peripheral nerve block quality. However, few reports have been published determining whether ultrasound can facilitate continuous nerve blocks. In this study, we tested the hypothesis that the addition of ultrasound to nerve stimulation facilitates femoral nerve blocks with a stimulating catheter.

Methods: In this prospective randomized study, patients receiving continuous femoral nerve blocks for total knee replacement were randomly assigned to either the ultrasound guidance combined with stimulating catheter group (USNS group; n = 60) or the stimulating catheter alone group (NS group; n = 60). The primary end point was the procedure time (defined as the time from first needle contact with the skin until correct catheter placement). The numbers of needle passes and catheter insertions, onset and quality of femoral nerve blocks, postoperative pain score, and early knee function were also recorded.

Results: The procedure time was significantly less in the USNS group than in the NS group (9.0 (6.0 - 22.8) minutes vs. 13.5 (6.0 - 35.9) minutes, P = 0.024). The numbers of needle passes and catheter insertions were also significantly less in the USNS group. A greater complete block rate was achieved at 30 minutes in the USNS group (63.3% vs. 38.3%; P = 0.010). The postoperative pain score, the number of patients who required bolus local anesthetic and intravenous patient-controlled analgesia, and knee flexion on the second postoperative day were not significantly different between the two groups of patients.

Conclusions: Ultrasound-assisted placement of a stimulating catheter for femoral nerve blocks decreases the time necessary to perform the block compared with just the nerve-stimulating technique. In addition, a more complete blockade is achieved using the ultrasound-assisted technique.
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February 2011

[Synthesis of 2-amino-4, 5-diarylpyrimidines and their protective effects against oxygen-glucose deprivation in PC12 cells].

Yao Xue Xue Bao 2010 Sep;45(9):1123-7

Key Laboratory of Ministry of Education for Medicinal Resource and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drug in Northwest of China, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an 710062, China.

A series of 6 novel 2-amino-4, 5-diarylpyrimidines were synthesized by the reaction of isoflavones with guanidine. They were identified by the spectra of IR, 1H NMR, 13C NMR and elemental analysis. The protective effects of 2-amino-4, 5-diarylpyrimidines against oxygen-glucose deprivation leading by sodium hydrosulfite in PC12 cells were studied by MTT method. It was shown that 2-amino-4, 5-diarylpyrimidines exhibited neuroprotective effects against oxygen-glucose deprivation injury in PC12 cells, which could increase the amount of survival PC12 cells and reduce their injured degree in the model.
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September 2010

[A case report of a successfully rescued patient with respiratory failure in late pregnancy].

Beijing Da Xue Xue Bao Yi Xue Ban 2010 Oct;42(5):586-90

Department of Anesthesiology, Peking University Third Hospital, Beijing 100191, China.

Respiratory problem is a common concomitant disease during pregnancy. Puerpera with respiratory failure has a high risk of morbidity and mortality. During pregnancy, a puerpera usually experienced obvious respiratory changes, which make the mother carry out enough oxygen to provide the fetus and meet its increasing need, and ensure that the mother will remove the excess of carbon dioxide produced by the elevated metabolic demands as the fetus grows mature. The normal value of arterial carbon dioxide tension(PaCO2 )is around 28 to 34 mmHg during noncomplicated pregnancies. The case we reported here was a 26-year-old woman, with G1P0. Emergency admission to Peking University Third Hospital because of chest suffocating for about 6 months. She was diagnosed as "Intrauterine pregnancy over 34 weeks, with respiratory failure type II and acidosis". The PaCO2 of the puerpera reached 74 mmHg before delivery and 94 mmHg after delivery. The doctors from several departments conducted cooperative management, undertook combined spinal and epidural anesthesia in the sitting position, controlled the anesthesia level and applied low concentration oxygen therapy. The baby was delivered successfully and the mother's condition was kept stable. Both the mother and the baby were discharged safely 11 days after operation. Although we carried out a series of checks, the exact cause of the disease remained unclear.
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October 2010
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