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

Article abstract of DOI:10.1246/cl.1991.1555

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.