Patent ID: 6844448
Filing Date: 2005-01-18
Classification: B01J,C07B,C07C

Abstract:
1. A process of stereoselective chemical synthesis which comprises reacting a π-bond-containing substrate represented by the general formula 1 and a nucleophile represented by NuY in the presence of a chiral, non-racemic catalyst to produce a stereoisomerically-enriched addition product 2, wherein said chiral, non-racemic catalyst comprises an asymmetric tetradentate ligand complexed with a main-group metal atom from Group 2, 12, 13, or 14; said catalyst having a rectangular planar or rectangular pyramidal geometry, and said process is represented by: wherein R, R′, and R″ represent, independently for each occurrence, hydrogen, alkyl, alkenyl, alkynyl, thioacyl, alkylthio, imine, phosphoryl, phosphonate, phosphine, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, heteroalkyl, amidine, acetal, ketal, aryl, heteroaryl, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, —C(O)R R R R X is selected from the group consisting of C(R) Y is selected, independently for each occurrence, from the group consisting of H, Li, Na, K, Ma, Ca, B, Al, Cu, Ag, Ti, Zr, Si(R) Nu is selected from the group consisting of conjugate bases of weak Bronsted acids and carbanions; R m represents independently for each occurrence an integer in the range 0 to 8 inclusive; and said chiral, non-racemic catalyst is represented by general formula 100; wherein Z the C R R or any two or more of R with the proviso that C M represents a main-group metal atom from Group 2, 12, 13 or 14; A represents a counterion or a nucleophile; and each of R