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

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. Exce...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-05, Vol.79 (9), p.4186-4195
Main Authors: Fontenelle, Clément Q, Conroy, Matthew, Light, Mark, Poisson, Thomas, Pannecoucke, Xavier, Linclau, Bruno
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500396p