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; Guigen Li

doi:10.1021/ol020146y

A new halo aldol reaction: three-component reaction via 1,4-robust activation of ethynyl alkyl ketones for stereoselective formations of versatile aldol adducts

Org Lett. 2002 Oct 17;4(21):3691-3. doi: 10.1021/ol020146y.

Authors

Han-Xun Wei¹, Sun Hee Kim, Guigen Li

Affiliation

¹ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.

PMID: 12375920
DOI: 10.1021/ol020146y

Abstract

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

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Aldehydes / chemistry*
Ketones / chemistry*
Stereoisomerism

Substances

Aldehydes
Ketones
3-hydroxybutanal

Grants and funding

GM-R15-60261/GM/NIGMS NIH HHS/United States