Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds

Bao Min Wang; Zhen Lei Song; Chun An Fan; Yong Qiang Tu; Wei Ming Chen

doi:10.1055/s-2003-40855

LETTER

Halogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds

Bao Min Wang, Zhen Lei Song, Chun An Fan, Yong Qiang Tu*, Wei Ming Chen
Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
Fax: +86(931)8912582; e-Mail: tuyq@lzu.edu.cn;

Abstract

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Abstract

Allylic alcohols were found to undergo a semipinacol-type rearrangement induced by halogen cation generated from the chloramine-T/ZnX₂ combination, which provided a highly efficient and stereoselective method for the preparation of α-quaternary β-haloketo compounds. This reaction is valuable and versatile since a quaternary carbon could be constructed effectively and three kinds of β-haloketo compounds (X = Cl, Br, I) could be achieved readily.

Key words

alcohols - halogenation - rearrangements - oxidations - zinc

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