A New Halo Aldol Reaction: Three-Component Reaction via 1,4-Robust Activation of Ethynyl Alkyl Ketones for Stereoselective Formations of Versatile Aldol Adducts

Han-Xun Wei, Sun Hee Kim, and Guigen Li*

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, Email: guigen.littu.edu

H.-X. Wei, S. H. Kim, G. Li, Org. Lett., 2002, 4, 3691-3693.

DOI: 10.1021/ol020146y

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Abstract

A new, diastereoselective three-component halo aldol reaction has been discovered for the tandem formations of I-C/C-C bonds, which gives aldol adducts in good yields. The key intermediates (allenolates and 1-iodo-3-siloxy-1,3-butadienes) were directly monitored by ¹H NMR.

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Key Words

Mukaiyama Aldol Addition, β-hydroxy ketones, vinyl iodides

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ID: J54-Y2002-390