Abstract-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.

Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with EthylBromodifluoroacetate with -Oxygenated Sulfinylimines. -The Honda--Reformatsky reaction involving bromodifluoroacetate (II) is investigated with both sulfinylimines derived from aliphatic aldehydes as well as those derived from aldehydes bearing a chiral -oxygenated substituent. The Reformatsky reaction of the latter proceeds with double diastereodifferentiation, with the configuration of the chiral sulfoxide determining the stereoinduction. On the contrary, sulfinylimines derived from unsubstituted alkanals react with virtually no diastereoselectivity. -(FONTENELLE, C. Q.; CONROY, M.; LIGHT, M.; POISSON, T.; PANNECOUCKE, X.; LINCLAU*, B.; J. Org. Chem. 79 (2014) 9, 4186-4195, http://dx.doi.org/10.1021/jo500396p ; Dep. Chem., Univ. Southampton, Southampton SO17 1BJ, UK; Eng.) -H. Haber 39-033