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Synlett 2003(10): 1497-1499
DOI: 10.1055/s-2003-40855
DOI: 10.1055/s-2003-40855
LETTER
© Georg Thieme Verlag Stuttgart ˙ New YorkHalogen Cation Induced Stereoselective Semipinacol-type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds
Further Information
Received
26 April 2003
Publication Date:
24 July 2003 (online)
Publication History
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.
Key words
alcohols - halogenation - rearrangements - oxidations - zinc
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