Stereochemical Control in Reactions of Chiral Ketone with 2‐Lithiated Substituted Ferrocene Derivatives.

Abstract

Organo-iron compounds Organo-iron compounds S 7100Stereochemical Control in Reactions of Chiral Ketone with 2-Lithiated Substituted Ferrocene Derivatives. -The addition of planar chiral 1-substituted 2-lithioferrocenes (I) and (VI) towards racemic α-substituted ketone (II) proceeds with formation of a new stereocenter with high stereoselectivity. Thus, two out of four possible diastereomers are obtained for the addition of ferrocene containing an electron-donating methyl group (I), while a single diastereomer is obtained for the ferrocene containing the electron-withdrawing chloro group (VI). Ionic hydrogenations of the major (RPlanar,S,R)-diastereomer of (III) and single diastereomer (X) proceed with moderate diastereoselectivity. -(TROITSKAYA*, L. L.; DEMESHCHIK, T. V.; OVSEENKO, S. T.; STARIKOVA, Z. A.; SOKOLOV, V. I.; MALEZIEUX, B.; GRUSELLE, M.; Russ. Chem. Bull. 52 (2003) 3, 616-623; Nesmeyanov Inst. Organoelem. Compd., Russ. Acad. Sci., Moscow 117813, Russia; Eng.) -Mischke 41-181