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A new synthesis of β,γ-unsaturated esters and allenic esters with construction of a carbon–carbon bond between α- and β-positions by the reaction of magnesium alkylidene carbenoids with lithium ester enolates

✍ Scribed by Tsuyoshi Satoh; Hiroaki Kaneta; Ayako Matsushima; Masanobu Yajima

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
748 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of lithium ester enolates with magnesium alkylidene carbenoids, generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride via the sulfoxide-magnesium exchange reaction, gave b,c-unsaturated esters in moderate to good yields. When this reaction was conducted with the lithium ester enolates of a-chlorocarboxylic acid esters, allenic esters were obtained. This procedure provides an unprecedented way for the synthesis of b,c-unsaturated esters and allenic esters from ketones with the construction of a carbon-carbon bond between aand b-positions.

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