Synlett 2003(10): 1497-1499
DOI: 10.1055/s-2003-40855
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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;
Further Information

Publication History

Received 26 April 2003
Publication Date:
24 July 2003 (online)

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.

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