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O-Silylated enolates in organic synthesis: α-Alkylation of carbonyl compounds by 1,3-dithienium fluoroborate.

✍ Scribed by Ian Paterson; Lee G. Price

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
224 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

S7.4mmary: The O-silylated enolates of ketones, aldehydes, esters, and lactones can be regiospecifically alkylated by 1,3-dithienium fluoroborate to give the selectivity protected S-dicarbonyl compounds.

We have found that the reaction of O-silylated enolates with a-chloroalkyl phenyl sulphides (PhSCHClR) is a useful method for the regiospecific a-alkylation and alkylidenation of carbonyl compounds."' This phenylthioalkylation reaction usually requi.res the presence of a suitable Lewis acid (e.g. ZnBr2, TiC14, or (PriO),TiC1,), and presumably involves the generation of an intermediate thiocarbocation, or an undissociated complex between the reagent and the Lewis acid, as the reacting electrophile. As an extension of this work, we were interested in examining the direct reaction of O-silylated enolates3 with some stable thiocarbocations. 4

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