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[HCo(CO) 4 ]‐Catalyzed Three‐component Cycloaddition of Epoxides, Imines, and Carbon Monoxide: Facile Construction of 1,3‐Oxazinan‐4‐ones
Author(s) -
Liu Lixia,
Sun Huailin
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403998
Subject(s) - carbon monoxide , cycloaddition , epoxide , chemistry , catalysis , imine , ring (chemistry) , component (thermodynamics) , monoxide , bar (unit) , organic chemistry , physics , thermodynamics , meteorology
Abstract The three‐component [3+2+1] cycloaddition of epoxides, imines, and carbon monoxide to produce 1,3‐oxazinan‐4‐ones has been developed by using [HCo(CO) 4 ] as the catalyst. The reaction occurs for a wide variety of imines and epoxides, under 60 bar of CO pressure at 50 °C, to produce 1,3‐oxazinan‐4‐ones with different substitution patterns in high yields, and provides an efficient and atom‐economic route to heterocycles from simple and readily available starting materials. A plausible mechanism involves [HCo(CO) 4 ]‐induced ring‐opening of the epoxide, followed by sequential addition of carbon monoxide and the imine, and then ring closure to form the product accompanied by regeneration of [HCo(CO) 4 ].