The Journal of Organic Chemistry

Silyl group-transfer-mediated serial Michael additions

PG Klimko, DA Singleton

Index: Klimko, Peter G.; Singleton, Daniel A. Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1733 - 1740

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Citation Number: 27

Abstract

Three protocols have been developed for achieving ordered, multiple (serial) Michael reactions initiated by silyl enol ethers or silyl ketene acetals. Anion (fluoride or m- chlorobenzoate) catalysis was most effective for reactions of silyl ketene acetal 2 with bis diesters, aa in the highly selective formation of 3. Lewis acid (ZnIz) catalysis was more general than anion catalysis and afforded stereochemically complementary products with ...