An efficient synthesis of cyclic urethanes from Boc-protected amino acids through a metal triflate-catalyzed intramolecular diazocarbonyl insertion reaction

JC Jung, MA Avery

Index: Jung, Jae-Chul; Avery, Mitchell A. Tetrahedron Letters, 2006 , vol. 47, # 45 p. 7969 - 7972

Full Text: HTML

Citation Number: 17

Abstract

A simple and efficient synthesis of cyclic urethanes and related oxazinanones 1a–l from diazoketones 3a–l is described. The transformation involves generation of carbenes by activation of diazo groups using metal triflates in intramolecular diazocarbonyl insertion reactions in high overall yields.