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Construction of enantiopure imine bridged benzo[c]azepinones by a silver(i) and chiral N-heterocyclic carbene multicatalytic reaction sequence of N′-(2-alkynylbenzylidene)hydrazides and cyclopropanecarbaldehydes

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Abstract

A novel and efficient method for the synthesis of enantiopure bridged benzo[c]azepinone compounds has been developed by metal/N-heterocyclic carbene multicatalysis. Catalyzed by CF3CO2Ag and a triazolium-derived chiral N-heterocyclic carbene in a cascade, the reaction between N′-(2-alkynylbenzylidene)hydrazides and cyclopropanecarbaldehydes proceeded efficiently under mild conditions to produce enantioselectively and diastereoselectively bridged heterocyclic compounds, (1R,4R,5S)-4-(acylethyl)-11-aryl-2-tosyl-1,2,4,5-tetrahydro-5,1-(azenometheno)benzo[c]azepin-3-ones, generally in good yields with 99–99.9% ee and 11 : 1–>50 : 1 dr.

Graphical abstract: Construction of enantiopure imine bridged benzo[c]azepinones by a silver(i) and chiral N-heterocyclic carbene multicatalytic reaction sequence of N′-(2-alkynylbenzylidene)hydrazides and cyclopropanecarbaldehydes

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Article information


Submitted
23 Jul 2020
Accepted
07 Sep 2020
First published
08 Sep 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Construction of enantiopure imine bridged benzo[c]azepinones by a silver(I) and chiral N-heterocyclic carbene multicatalytic reaction sequence of N′-(2-alkynylbenzylidene)hydrazides and cyclopropanecarbaldehydes

J. Ma and Y. Cheng, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00877J

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