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 with bis diesters. Lewis acid (ZnI 2 ) catalysis was more general than anion catalysis and afforded stereochemically complementary products with lower selectivity. The use of SnCl 2 -trityl chloride was effective in reactions of both silyl ketene acetals and silyl enol ethers with bis enones

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