Chlorine, an atom economical auxiliary for asymmetric aldol reactions.
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.
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada, V55 1S6.
Shira D
SD
Halperin
Robert
R
Britton
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D054879:Halogenation; D015394:Molecular Structure
D000438:Alcohols; D000447:Aldehydes; D002713:Chlorine