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J Am Chem Soc. 2008 Apr 23;130(16):5408-9. doi: 10.1021/ja800747m. Epub 2008 Apr 1.

Tandem Michael addition/ylide epoxidation for the synthesis of highly functionalized cyclohexadiene epoxide derivatives.

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  • 1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 FengLin Lu, Shanghai 200032, China.

Abstract

A highly efficient diastereoselective synthesis of cyclohexadiene epoxide derivatives with a multi-stereocenter has been developed via a tandem ylide Michael addition/epoxidation. By employing a chiral sulfonium ylide, up to 96% ee can be achieved in good yields.

PMID:
18376828
[PubMed]
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