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Letter

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

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

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061

Org. Lett., 2002, 4 (21), pp 3691–3693

DOI: 10.1021/ol020146y

Publication Date (Web): September 25, 2002

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, qeggl@ttu.edu

Abstract

A new three-component halo aldol reaction has been discovered for the tandem formations of I−C/C−C bonds by activating the α‘,β-positions of α,β-acetylenic ketones. The key intermediates, 1-iodo-3-siloxy-1,3-butadienes, were generated from allenolates and directly monitored by ¹H NMR spectroscopic analysis. Excellent geometric selectivity (>95%) and good yields (65−82%) have been achieved for 10 examples.

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Published In Issue October 17, 2002
Received July 30, 2002

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Letter

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Mechanistic Insights into the Catalytic Asymmetric Allylboration of Ketones: Brønsted or Lewis Acid Activation?

Total Synthesis of (−)-Acutumine

Palladium-Catalyzed, One-Pot, Three-Component Synthesis of Homoallylic Amines from Aldehydes, Anisidine, and Allyl Trifluoroacetate

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