Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with alpha-Oxygenated Sulfinylimines

作者:Fontenelle Clement Q; Conroy Matthew; Light Mark; Poisson Thomas*; Pannecoucke Xavier; Linclau Bruno
来源:Journal of Organic Chemistry, 2014, 79(9): 4186-4195.
DOI:10.1021/jo500396p

摘要

The Reformatsky reaction of ethyl bromodifluoroacetate to alpha-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (%26gt;94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity.

  • 出版日期2014-5-2