Synthesis of γ,δ-Unsaturated Selenoamides via the Seleno-Claisen Rearrangement of in situ Generated Allylic Vinyl Selenides from Selenoamides and Allylic Bromides­

Toshiaki Murai; Tatsuya Ezaka; Shinzi Kato

doi:10.1055/s-0032-1317149

Synthesis, Table of Contents

Synthesis 2012; 44(20): 3197-3201
DOI: 10.1055/s-0032-1317149

paper

Synthesis of γ,δ-Unsaturated Selenoamides via the Seleno-Claisen Rearrangement of in situ Generated Allylic Vinyl Selenides from Selenoamides and Allylic Bromides

Toshiaki Murai*

Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan Fax: +81(58)2932614 Email: mtoshi@gifu-u.ac.jp

,

Tatsuya Ezaka

Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan Fax: +81(58)2932614 Email: mtoshi@gifu-u.ac.jp

,

Shinzi Kato

Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan Fax: +81(58)2932614 Email: mtoshi@gifu-u.ac.jp

› Author Affiliations

Abstract

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Abstract

The deprotonation of α-monosubstituted selenoamides with LDA followed by allylation gives γ,δ-unsaturated selenoamides in good to high yields. In the initial step, allylation may take place at the selenium atom of lithium eneselenolates to form allylic vinyl selenides, which then undergo seleno-Claisen rearrangement. As allylic bromides, γ,γ-disubstituted compounds such as geranyl and neryl bromides could also be used to give products that incorporated tertiary-quaternary stereogenicity with high efficiency.

Key words

seleno-Claisen rearrangement - γ,δ-unsaturated selenoamides - tertiary-quaternary stereogenicity - high stereoselectivity

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References

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Synthesis of γ,δ-Unsaturated Selenoamides via the Seleno-Claisen Rearrangement of in situ Generated Allylic Vinyl Selenides from Selenoamides and Allylic Bromides­

Synthesis of γ,δ-Unsaturated Selenoamides via the Seleno-Claisen Rearrangement of in situ Generated Allylic Vinyl Selenides from Selenoamides and Allylic Bromides