A new synthesis of beta,gamma-unsaturated esters and allenic esters with construction of a carbon-carbon bond between alpha- and beta-positions by the reaction of magnesium alkylidene carbenoids with lithium ester enolates

作者：Satoh Tsuyoshi^*; Kaneta Hiroaki; Matsushima Ayako; Yajima Masanobu

来源：Tetrahedron Letters, 2009, 50(46): 6280-6285.

DOI：10.1016/j.tetlet.2009.08.102

• Magnesium carbenoid
• Magnesium alkylidene carbenoid
• Sulfoxide-magnesium exchange reaction
• beta,gamma-unsaturated ester
• Allenic ester

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 beta,gamma-unsaturated esters in moderate to good yields. When this reaction was conducted with the lithium ester enolates of alpha-chlorocarboxylic acid esters, allenic esters were obtained. This procedure provides an unprecedented way for the synthesis of beta,gamma-unsaturated esters and allenic esters from ketones with the construction of a carbon-carbon bond between alpha- and beta-positions.

• 出版日期2009-11-18