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Issue 20, 2020
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Enantioselective dearomative [3 + 2] annulation of 3-hydroxy chromanones with azonaphthalenes

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Abstract

Enantioselective dearomative [3 + 2] annulation of 3-hydroxy chromanones with azonaphthalenes was realized using a chiral squaramide-tertiary amine as a catalyst. A large variety of chromanone fused indolines were obtained in moderate to good yields (up to 93%) with generally good enantioselectivities (up to 95% ee). The absolute configuration of one of the products was assigned by an X-ray crystal structural analysis, and a plausible reaction mechanism was proposed. Afterwards, two arylated derivatives were prepared by the Suzuki–Miyaura coupling of one of the products with aryl boronic acids.

Graphical abstract: Enantioselective dearomative [3 + 2] annulation of 3-hydroxy chromanones with azonaphthalenes

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Supplementary files

Article information


Submitted
30 Jun 2020
Accepted
23 Aug 2020
First published
27 Aug 2020

Org. Chem. Front., 2020,7, 3160-3165
Article type
Research Article

Enantioselective dearomative [3 + 2] annulation of 3-hydroxy chromanones with azonaphthalenes

J. Zhang, M. Liu, M. Huang, H. Liu, Y. Yan, Z. Wang and X. Zhang, Org. Chem. Front., 2020, 7, 3160
DOI: 10.1039/D0QO00772B

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