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

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journal contribution
posted on 21.08.2015, 00:00 by Motoyuki Isoda, Kazuyuki Sato, Masato Funakoshi, Keiko Omura, Atsushi Tarui, Masaaki Omote, Akira Ando
The combination of Et2Zn and RhCl­(PPh3)3 led to the facile generation of a rhodium–hydride complex (Rh–H) that catalyzed the 1,4-reduction of α,β-unsaturated esters. The resulting rhodium enolate performed as a Reformatsky-type reagent and reacted with various imines to give syn-β-lactams in good to excellent yields with high diastereoselectivity.