Broad-spectrum enantioselective Diels-Alder catalysis by chiral, cationic oxazaborolidines

DH Ryu, TW Lee, EJ Corey

Index: Corey; Shibata, Takanori; Lee, Thomas W. Journal of the American Chemical Society, 2002 , vol. 124, # 15 p. 3808 - 3809

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Citation Number: 170

Abstract

The cationic chiral Lewis acids 1 and 2, generated by triflic acid protonation of the corresponding neutral oxazaborolidines, serve as excellent catalysts for Diels-Alder addition of cyclopentadiene to a wide variety of dienophiles. Adducts have been obtained in excellent yield and enantioselectivity from α, β-unsaturated esters, lactones, and cyclic ketones. The absolute facial selectivity for each of these substrates follows a common ...

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