Journal
ORGANIC LETTERS
Volume 16, Issue 9, Pages 2482-2485Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol500856z
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- BRL (Basic Research Laboratory) program of the National Research Foundation (NRF) - Korean government
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A rhodium-catalyzed oxygenative [2 + 2] cycloaddition of terminal alkynes and imines has been developed, which gives beta-lactams as products with high trans diastereo-selectivity. In the presence of a Rh(I) catalyst and 4-picoline N-oxide, a terminal alkyne is converted to a rhodium ketene species via oxidation of a vinylidene complex and subsequently undergoes a [2 + 2] cycloaddition with an imine to give rise to the 2-azetidinone ring system. Mechanistic studies suggest that the reaction proceeds through a metalloketene rather than free ketene intermediate. The new method taking advantage of catalytic generation of a ketene species directly from a terminal alkyne provides a novel and efficient entry to the Staudinger synthesis of beta-lactams under mild conditions.
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