Stereoselective Synthesis of α,β-Epoxy Ketones by the Darzen's Reaction  with Methyl N-Ethyl-N-tributylstannylcarbamate

Ikuya Shibata; Hayahide Yamasaki; Akio Baba; Haruo Matsuda

doi:10.1055/s-1990-21139

Synlett 1990; 1990(8): 490-492
DOI: 10.1055/s-1990-21139

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Stereoselective Synthesis of α,β-Epoxy Ketones by the Darzen's Reaction with Methyl N-Ethyl-N-tributylstannylcarbamate

Ikuya Shibata^* , Hayahide Yamasaki, Akio Baba, Haruo Matsuda

^*Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565, Japan

Abstract

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Methyl N-ethyl-N-tributylstannylcarbamate is shown to be an efficient reagent for the Darzen's reaction. Its reactivity is increased by the addition of equimolar amounts of hexa-methylphosphoric triamide. The stereoselectivity of the product is controlled by the conditions, such as the halogen group of the substrate and the presence of hexamethylphosphoric triamide. This method is the first example of the stereoselective synthesis of cis-epoxy ketones by a one-pot Darzen's reaction of α-halo ketones and aldehydes.

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