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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Organic & Biomolecular Chemistry
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