Jump to main content
Jump to site search

Issue 10, 2013
Previous Article Next Article

Chlorine, an atom economical auxiliary for asymmetric aldol reactions

Author affiliations

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.

Graphical abstract: Chlorine, an atom economical auxiliary for asymmetric aldol reactions

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Dec 2012, accepted on 10 Jan 2013 and first published on 31 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB27462D
Citation: Org. Biomol. Chem., 2013,11, 1702-1705
  •   Request permissions

    Chlorine, an atom economical auxiliary for asymmetric aldol reactions

    S. D. Halperin and R. Britton, Org. Biomol. Chem., 2013, 11, 1702
    DOI: 10.1039/C3OB27462D

Search articles by author

Spotlight

Advertisements