Synthesis of boroles and their use in low-temperature Diels-Alder reactions with unactivated alkenes

PJ Fagan, EG Burns, JC Calabrese

Index: Fagan, Paul J.; Burns, Elizabeth G.; Calabrese, Joseph C. Journal of the American Chemical Society, 1988 , vol. 110, p. 2979 - 2981

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Citation Number: 75

Abstract

Steric enhancement of rate is unprecedented in group transfer reactions such as epoxidation, and this selectivity cannot be rationalized in terms of inductive differences, since no such effect is manifested in the re1 kmeBA experiments. However, completely analogous steric effects on the rates of epoxidation of fast and slow enantiomers had been seen previously with respect to increasing size of the tartrate ester group. Ibsd Although ...