Enantioselective reformatsky reaction of methyl bromodifluoroacetate

✍ Scribed by Braun, Manfred ;Vonderhagen, Anja ;Waldmüller, Delia

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 386 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199508196

✦ Synopsis

Abstract

The Reformatsky reagent 2 generated from methyl bromodifluoroacetate is added to benzaldehyde in the presence of carbinols 3a, b, amino alcohols 3c‐g, or amino alkoxide 3h. N‐Methylephedrine 3c provides the highest enantioselectivity in the formation of the adduct S‐4a (84% ee; >96% after recrystallization) whose absolute configuration is determined by an X‐ray structural analysis of the amide 6.