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Rapid assembly of cyclopentene spiroisoindolinones via a rhodium-catalysed redox-neutral cascade reaction

Author:
Yuan, Tingting, Pi, Chao, You, Chang, Cui, Xiuling, Du, Sidong, Wan, Ting, Wu, Yangjie
Source:
Chemical communications 2018 v.55 no.2 pp. 163-166
ISSN:
1364-548X
Subject:
aromatic compounds, benzamides, byproducts, carbon, chemical bonding, chemical reactions, moieties
Abstract:
An unprecedented strategy of a rhodium-catalysed redox-neutral cascade reaction starting from benzamides and cyclopropenones via addition of a C–H bond into a polar carbonyl group for the rapid assembly of cyclopentene spiroisoindolinones has been developed. Water was produced as the sole by-product. Metal migration and abstraction of a H-atom from the arylcyclopropenone's aromatic ring are the key steps in building the spirocycle. Two C–C bonds, one C–N bond and an N-substituted quaternary carbon center were formed sequentially in a one pot manner.
Agid:
6266306