Electronic polarizability-based stereochemical model for Sharpless AD reactions

Abstract

Softness really is the hard force! Reported here was the critical yet long-overlooked role of electronic polarizability (i.e., softness) effect in controlling absolute stereochemical courses of general asymmetric induction events. Thus, a sensitive dependence of the sense of chiral induction on an alkene substrate's substituent electronic polarizability character was uncovered from a range of structurally highly comparable Sharpless asymmetric dihydroxylation (AD) systems, from which a new polarizability-based stereochemical model of predictive power was suggested. © 2011 Elsevier Ltd. All rights reserved.