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Communication | Special issue | Vol 73, No. 1, 2007, pp.203-208
Published online, 10th August, 2007
DOI: 10.3987/COM-07-S(U)29
The Diastereoselective Synthesis of Difluoro-β-lactam Using Reformatsky-Honda Reaction

Atsushi Tarui, Keigo Kondo, Hiroko Taira, Kazuyuki Sato, Masaaki Omote, Itsumaro Kumadaki, and Akira Ando*

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka, 573-0101, Japan

Abstract

The high diastereoselective synthesis of chiral difluoro-β-lactams (3) was attained by treatment of ethyl bromodifluoroacetate (1), 2-hydroxy-1-phenylethyl group substituted imines (2) and diethylzinc in the presence of rhodium-catalyst. The absolute configuration of 3 was determined by X-ray analysis of 3,5-dinitrobenzoate (6) derived from 3.