Reversal of Diastereofacial Selectivity in the Addition Reaction of Organometallics to Chiral Imines.

It was observed that diastereofacial selectivity in the addition reaction of organometallics to the chiral imines derived from (R)-2-methoxy-1-phenylethylamine was regulated under appropriate conditions; i. e., organolithium and organocerium reagents added from the re-face of the chiral imines selectively, while organocopper reagents attacked from the si-face. The utility of the present method was demonstrated in the enantioselective synthesis of solenopsin A.