Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with ?-oxygenated sulfinylimines

• Main Authors: Fontenelle, Clément Q. (Author), Conroy, Matthew (Author), Light, Mark (Author), Poisson, Thomas (Author), Pannecoucke, Xavier (Author), Linclau, Bruno (Author)
• Format: Article
• Language: English
• Published: 2014.
• Subjects: Article
• Online Access: Get fulltext

The Reformatsky reaction of ethyl bromodifluoroacetate to ?-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