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Synlett 2009(5): 724-726  
DOI: 10.1055/s-0028-1087930
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Preparation of 3-Alkanoylprop-2-en-1-ol Derivatives

Mutsumi Sada, Shizue Ueno, Keisuke Asano, Kenichi Nomura, Seijiro Matsubara*
Department of Material Chemistry, Kyoto University, Kyoutodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan
Fax: +81(75)3832459; e-Mail: matsubar@orgrxn.mbox.media.kyoto-u.ac.jp;
Further Information

Publication History

Received 10 November 2008
Publication Date:
24 February 2009 (online)

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Abstract:

3-Alkanoylprop-2-en-1-ol derivatives were prepared stereoselectively by ring-opening reaction of β,γ-epoxyketone with amines.

Key words

epoxide - amine - enone - rearrangement - alcohol

    References and Notes

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6

The reaction was monitored by ¹H NMR for 2 h using CD2Cl2 as solvent. Through the whole reaction, Z-form was not detected in the product.

7

From a ¹H NMR analysis, 4 was considered to have Z-configuration. Alkenoic proton was detected at δ = 6.34 ppm. See experimental procedure.