Organic & Biomolecular Chemistry 2014-09-07

Enantioselective synthesis of α,α-difluoro-β-lactams using amino alcohol ligands.

Atsushi Tarui, Takeshi Ikebata, Kazuyuki Sato, Masaaki Omote, Akira Ando

Index: Org. Biomol. Chem. 12(33) , 6484-9, (2014)

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Abstract

A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described. A variety of α,α-difluoro-β-lactams were obtained in up to 74% yield with high enantioselectivity in excess of 99% ee. The use of ethyl bromodifluoroacetate provides for ease of operation because of the inherent chemical stability of this reagent.