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Synlett 1998; 1998(9): 987-988
DOI: 10.1055/s-1998-5739
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Asymmetric [2,3]Sigmatropic Rearrangement of Optically Active Allylic Selenides

Ken-ichi Fujita* , Mitsuhiro Kanakubo, Hirobumi Ushijima, Akihiro Oishi, Yoshikazu Ikeda, Yoichi Taguchi
  • *National Institute of Materials and Chemical Research, 1-1, Higashi, Tsukuba, Ibaraki 305-8565, Japan; Fax +81-298-54-4511; E-mail: kfujita@nimc.go.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Oxidation of an optically active allylic selenide derived from l-proline 1 with m-chloroperbenzoic acid afforded the corresponding chiral allylic alcohol 3 via asymmetric [2,3]sigmatropic rearrangement with fair enantioselectivity (up to 66% e.e.).

asymmetric [2,3]sigmatropic rearrangement - Se ⋅ ⋅ ⋅ N interaction - optically active allylic selenide - chiral selenoxide