ChemInform Abstract: Stealth Stereocontrol. Stereochemical Reversal of a Michael Addition Reaction.

Abstract

Reversal of a Michael AdditionReaction.-The Michael addition of nucleophiles of type (II) and (IV) to the furanoside (I) proceeds in a highly stereoselective manner but with different stereochemical outcome compared to the Michael addition of aerofoil-shaped nucleophiles such as (VI) and (VIII). This unexpected reversal of relative asymmetric induction is ascribed to the effect exerted by the wing tip carbonyls of (VI) and (VIII). This effect is termed as stealth stereocontrol. -(BARRETT, A. G. M.; WEIPERT, P. D.; DHANAK, D.; HUSA, R. K.; LEBOLD, S. A.; J. Am. Chem. Soc. 113 (1991) 26, 9820-9824; Dep. Chem., Colo. State Univ., Fort Collins, CO 80523, USA; EN)