Gold-Catalyzed Efficient Preparation of Linear α-Iodoenones from Propargylic Acetates

Meng Yu, Guozhu Zhang and Liming Zhang*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA 93106-9510, Email: zhangchem.ucsb.edu

M. Yu, G. Zhang, L. Zhang, Org. Lett., 2007, 9, 2087-2090.

DOI: 10.1021/ol070637o (free Supporting Information)

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Abstract

A catalytic amount of Au(PPh₃)NTf₂ converts readily accessible propargylic acetates into versatile linear α-iodoenones in good to excellent yields. Very good Z-selectivities are observed for aliphatic propargylic acetates.

see article for more examples

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Practical Synthesis of Linear α-Iodo/Bromo-α,β-unsaturated Aldehydes/Ketones from Propargylic Alcohols via Au/Mo Bimetallic Catalysis

L. Ye, L. Zhang, Org. Lett., 2009, 11, 3646-3649.

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Key Words

Propargylic Alcohols, Iodination, Enones, NIS

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ID: J54-Y2007-1720