New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines

Cody Timmons, Dianjun Chen, John F. Cannon, Allan D. Headley, Guigen Li

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

Equation presented. A new asymmetric halo aldol reaction has been developed by reacting cyclopropyl carbonyl derived enolates with aldehydes. The absolute structure was unambiguously confirmed by X-ray structural analysis. Eight examples were reported with good yields and up to complete control of diastereomeric excesses. These halo aldol products have been readily cyclized in the presence of weak bases to produce chiral 2,3-disubstituted tetrahydrofuran derivatives in good yield without any observed epimerization.

Original languageEnglish
Pages (from-to)2075-2078
Number of pages4
JournalOrganic Letters
Volume6
Issue number12
DOIs
StatePublished - Jun 10 2004

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