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Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction.

ABSTRACT: A catalytic asymmetric method for the synthesis of polysubstituted chromans via an oxa-Michael-nitro-Michael reaction has been developed. The squaramide-catalyzed domino reaction of 2-hydroxynitrostyrenes with trans-β-nitroolefins produced chiral chromans with excellent enantioselectivities (up to 99% ee), diastereoselectivities (up to >20 : 1 dr), and moderate to good yields (up to 82%).

SUBMITTER: Tang CK

PROVIDER: S-EPMC9077565 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction.

Tang Cheng-Ke CK Feng Kai-Xiang KX Xia Ai-Bao AB Li Chen C Zheng Ya-Yun YY Xu Zhen-Yuan ZY Xu Dan-Qian DQ

RSC advances 20180117 6

A catalytic asymmetric method for the synthesis of polysubstituted chromans via an oxa-Michael-nitro-Michael reaction has been developed. The squaramide-catalyzed domino reaction of 2-hydroxynitrostyrenes with trans-β-nitroolefins produced chiral chromans with excellent enantioselectivities (up to 99% ee), diastereoselectivities (up to >20 : 1 dr), and moderate to good yields (up to 82%). ...[more]

PMID: 35541173

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