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Updated: May 14, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Chlorine, an atom economical auxiliary for asymmetric aldol reactions
Shira D Halperin1, Robert Britton
1Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada, V55 1S6.
Abstract:
An auxiliary strategy has been developed for asymmetric reactions of aldehydes in which the auxiliary itself is not chiral, but a single chlorine atom introduced via organocatalytic α-chlorination. The stereodirecting influence of the chlorine atom is then exploited prior to its removal by radical reduction. This strategy is demonstrated in the synthesis of several aldols (92-99% ee) and the natural products (+)-dihydroyashabushiketol and (+)-solistatin.
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