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Stereoselectivity of the Honda–Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α‑Oxygenated Sulfinylimines

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posted on 2014-05-02, 00:00 authored by Clément Q. Fontenelle, Matthew Conroy, Mark Light, Thomas Poisson, Xavier Pannecoucke, Bruno Linclau
The Reformatsky reaction of ethyl bromodifluoroacetate to α-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 (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity.

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