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Construction of 4‐Isochromanones through Cu(OTf) 2 ‐Catalysed Sequential C=O and C–O Bond Formation
Author(s) -
Xing Siyang,
Gu Nan,
Qin Jiajing,
Cui Hong,
Li Yan,
Wang Kui,
Tian Dawei,
Chen Bo,
Yu Guo
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701808
Subject(s) - chemistry , substrate (aquarium) , ring (chemistry) , solvent , scope (computer science) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , oceanography , geology , computer science , programming language
A new strategy for the facile and efficient synthesis of 4‐isochromanones has been developed. The reaction involves a Cu(OTf) 2 ‐catalysed sequential reaction of epoxides carrying electron‐deficient alkenes using the solvent DMSO as the oxidant. The single‐step process involves a sequential oxidative ring opening of epoxides and an oxa‐Michael addition where one new C=O bond and one new C–O bond are created. The advantages of this approach include high efficiency, a broad substrate scope, and mild conditions.
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