Synthesis of α,β-Unsaturated Selenoamides by the Condensation Reaction of Lithium Eneselenolate Generated from Selenoacetamide with Aldehydes

Toshiaki Murai; Tatsuya Ezaka; Toshio Ichimiya; Shinzi Kato

doi:10.1055/s-1997-5781

Synlett 1997; 1997(7): 775-776
DOI: 10.1055/s-1997-5781

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Synthesis of α,β-Unsaturated Selenoamides by the Condensation Reaction of Lithium Eneselenolate Generated from Selenoacetamide with Aldehydes

Toshiaki Murai^* , Tatsuya Ezaka, Toshio Ichimiya, Shinzi Kato

^*Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-11, Japan, Fax 58 230 1893; e-mail toshi@apchem.gifu-u.ac.jp

Abstract

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The reaction of lithium eneselenolate generated from selenoacetamide and LDA with aldehydes gave α,β-unsaturated selenoamides in good to high yields. The successive addition of n-butyllithium and 3-bromo-1-propene to α,β-unsaturated selenoamide 3a gave selenoamide 7 with high selectivity.

selenoacetamide - α,β-unsaturated selenoamides - aldol type condensation

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