A PhSeCl-Mediated Allylic Oxidation of Prenyl Moiety: A Convenient Method for the Construction of 3-Isopenten-2-ol Unit

Motoko Oshida; Tomoaki Nakamura; Atsuo Nakazaki; Susumu Kobayashi

doi:10.1248/cpb.56.404

Notes

A PhSeCl-Mediated Allylic Oxidation of Prenyl Moiety: A Convenient Method for the Construction of 3-Isopenten-2-ol Unit

Motoko Oshida, Tomoaki Nakamura, Atsuo Nakazaki, Susumu Kobayashi

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Keywords: allylic oxidation, trisubstituted alkene, sigmatropic rearrangement, phenylselenenyl chloride, prenyl moiety, 3-isopenten-2-ol

JOURNAL FREE ACCESS

2008 Volume 56 Issue 3 Pages 404-406

DOI https://doi.org/10.1248/cpb.56.404

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Abstract

A phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.

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