Asymmetric Synthesis of Triaryl‐Substituted Chromans with Multiple Stereogenic Centers by [4+2] Cycloaddition Reaction | Zendy

Zhang Heng | Zendy; Liu Guofeng | Zendy; Guan Xukai | Zendy; Gao Jigang | Zendy; Qin Xiangshuo | Zendy; Jiang Guofeng | Zendy; Sun Dongyang | Zendy; Zhang Guangliang | Zendy; Zhang Suoqin | Zendy

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Asymmetric Synthesis of Triaryl‐Substituted Chromans with Multiple Stereogenic Centers by [4+2] Cycloaddition Reaction

Author(s) -

Zhang Heng,

Liu Guofeng,

Guan Xukai,

Gao Jigang,

Qin Xiangshuo,

Jiang Guofeng,

Sun Dongyang,

Zhang Guangliang,

Zhang Suoqin

Publication year - 2019

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.201901286

Subject(s) - stereocenter , chemistry , cycloaddition , enantioselective synthesis , catalysis , stereochemistry , stereoselectivity , combinatorial chemistry , in situ , organic chemistry

Asymmetric synthesis of triaryl‐substituted chromans with multiple adjacent stereogenic centers is described here. [4+2] formal oxa ‐Diels‐Alder cycloaddition of 1‐styrylnaphthols and in‐situ‐generated o ‐quinone metheides could proceed smoothly in the presence of H 8 ‐BINOL‐type chiral imidodiphosphoric acids as catalyst. This method provides an efficient strategy to construct chiral chroman frameworks in high yields (up to 93 %) with excellent stereoselectivities (> 19:1 dr.) and enantioselectivities (up to 99 % ee ).

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