Dalton Trans 2021 Mar;50(9):3178-3185
Inorganic and Organometallic Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstraße 1, 91058 Erlangen, Germany.
The chiral building block (R)-(+)-2,2'-diamino-1,1'-binaphthyl, (R)-BINAM, which is often used as backbone in privileged enantioselective catalysts, was converted to a series of N-substituted proligands R1-H2 (R = CH2tBu, C(H)Ph2, PPh2, dibenzosuberane, 8-quinoline). After double deprotonation with strong Mg or Ca bases, a series of alkaline earth (Ae) metal catalysts R1-Ae·(THF)n was obtained. Crystal structures of these C2-symmetric catalysts have been analyzed by quadrant models which show that the ligands with C(H)Ph2, dibenzosuberane and 8-quinoline substituents should give the best steric discrimination for the enantioselective intramolecular alkene hydroamination (IAH) of the aminoalkenes H2C[double bond, length as m-dash]CHCH2CR'2CH2NH2 (CR'2 = CPh2, CCy or CMe2). Read More