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Synthesis 2018; 50(06): 1343-1349
DOI: 10.1055/s-0036-1589162
paper
© Georg Thieme Verlag Stuttgart · New York

Trimethylphosphine-Promoted Alcoholysis of α,β-Unsaturated Imides and α,β-Unsaturated Esters

Haruka Sato
Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan   Email: seijiro@waseda.jp
,
Seijiro Hosokawa*
Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan   Email: seijiro@waseda.jp
› Author AffiliationsThe authors are grateful for financial support from the Kurata Memorial Hitachi Science and Technology Foundation, the Naito Foundation, and the Sumitomo Foundation.
Further Information

Publication History

Received: 10 November 2017

Accepted after revision: 06 December 2017

Publication Date:
16 January 2018 (online)

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Abstract

α,β-Unsaturated imides and α,β-unsaturated esters were found to undergo alcoholysis in the presence of trimethylphosphine. The reaction is initiated by nucleophilic addition of trimethylphosphine to the double bond of the α,β-unsaturated carbonyl compound. Saturated imides also undergo the alcoholysis in the presence of the corresponding α,β-unsaturated imide.

Key words

trimethylphosphine - conjugate addition - alcoholysis - transesterification - unsaturated imides - unsaturated esters

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589162.
  • Supporting Information
 

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