Organic letters

Ruthenium-catalyzed stereoselective intramolecular carbenoid CH insertion for β-and γ-lactam formations by decomposition of α-diazoacetamides

MKW Choi, WY Yu, CM Che

Index: Choi, Matthew Kwok-Wai; Yu, Wing-Yiu; Che, Chi-Ming Organic Letters, 2005 , vol. 7, # 6 p. 1081 - 1084

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Citation Number: 69

Abstract

An operationally simple catalytic system based on [RuCl2 (p-cymene) 2] was developed for stereoselective cyclization of α-diazoacetamides by intramolecular carbenoid CH insertion, and β-lactams were produced in excellent yields and> 99% cis-stereoselectivity. The Ru- catalyzed reactions can be performed without the need for slow addition of diazo compounds and inert atmosphere. With α-diazoanilides as substrate, the carbenoid ...