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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 ).