Journal of Organic Chemistry p. 468 - 473 (1984)
Update date:2022-08-03
Topics:
Trost, Barry M.
Self, Christopher R.
Treatment of lithium enolates with trialkylstannyl trifluoroacetates permits their use as nucleophiles in allylic alkylations catalyzed by palladium with high regioselectivity and without polyalkylation.Alkylation without concomitant desilylation occurs for 3-acetoxy-1-(trimethylsilyl)-1-propene and n-butyl 2-acetoxy-4-(trimethylsilyl)-3-butenoate under these conditions.The choice of substituents on the tin does affect the rate of the alkylation; trimethyl substitution proceeds substantially faster than tri-n-butyl substitution.
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