Diastereo-and enantioselective aldehyde addition reactions of 2-allyl-1, 3, 2-dioxaborolane-4, 5-dicarboxylic esters, a useful class of tartrate ester modified …

WR Roush, AE Walts, LK Hoong

Index: Roush, William R.; Walts, Alan E.; Hoong, Lee K. Journal of the American Chemical Society, 1985 , vol. 107, # 26 p. 8186 - 8190

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Citation Number: 304

Abstract

Abstract: The preparation and aldehyde addition reactions of the title compounds (la-c) are described. These tartrate ester based reagents are the most highly enantioselective group of allylboronate esters reported to date. Reagent lb prepared from diisopropyl tartrate reacts with achiral aldehydes to give homoallylic alcohols in good yield and high enantioselectivity (7 1-87% ee). Interestingly, the greatest selectivity is obtained with a-branched aldehydes ...