jo500396p_si_001.pdf (6.21 MB)
Stereoselectivity of the Honda–Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α‑Oxygenated Sulfinylimines
journal contribution
posted on 2014-05-02, 00:00 authored by Clément
Q. Fontenelle, Matthew Conroy, Mark Light, Thomas Poisson, Xavier Pannecoucke, Bruno LinclauThe
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.