TiCl₄-n-Bu₄NX (X = I, Br, and Cl) Combination-Induced Coupling of α,β-Unsaturated Ketones with Aldehydes

Zhenfu Han, Shigeki Uehira, Hiroshi Shinokubo and Koichiro Oshima*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan

Z. Han, S. Uehira, H. Shinokubo, K. Oshima, J. Org. Chem., 2001, 66, 7854-7857.

DOI: 10.1021/jo016054o

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Abstract

Treatment of vinyl ketones with a combination of TiCl₄ and n-Bu₄NI followed by an addition of a variety of aldehydes provides syn-α-iodomethyl-β-hydroxy ketones with high stereoselectivity. The use of n-Bu₄NBr or n-Bu₄NCl provides the corresponding bromo or chloro compounds in good yields.

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Key Words

β-hydroxy ketones, β-bromoketones, β-iodoketones

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ID: J42-Y2001