Diastereoselective Synthesis of syn-β-Lactams Using Rh-Catalyzed Reductive Mannich-Type Reaction of α,β-Unsaturated Esters

Motoyuki Isoda, Kazuyuki Sato, Masato Funakoshi, Keiko Omura, Atsushi Tarui, Masaaki Omote and Akira Ando*

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan, Email: aandopharm.setsunan.ac.jp

M. Isoda, K. Sato, M. Funakoshi, K. Omura, A. Tarui, M. Omote, A. Ando, J. Org. Chem., 2015, 80, 8398-8405.

DOI: 10.1021/acs.joc.5b01233

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Abstract

A rhodium-hydride complex (Rh-H), generated from Et₂Zn and RhCl(PPh₃)₃, catalyzes a 1,4-reduction of α,β-unsaturated esters. The resulting rhodium enolate reacted as a Reformatsky-type reagent with various imines to give syn-β-lactams in good to excellent yields with high diastereoselectivity.

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Key Words

β-lactams

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ID: J42-Y2015