Synthesis of Trisubstituted Chromanes by Lewis-Base-Catalyzed Three-Component Electrophilic Thiofunctionalization of Cyclopropene with Phenols via a Formal [3+3] Annulation

被引：4
作者：
Liu, Bowen [1 ]
Wang, Lei [2 ]
Qin, Yunfei [1 ]
Xu, Xianxiu [2 ]
Zhao, Jinbo [1 ,3 ]
机构：
[1] Changchun Univ Technol, Jilin 130012, Shandong, Peoples R China
[2] Shandong Normal Univ, Coll Chem, Chem Engn & Mat Sci, Jinan 250014, Shandong, Peoples R China
[3] Shandong First Med Univ & Shandong Acad Med Sci, Sch Pharm, Tai An 271016, Shandong, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 31期
基金：
中国国家自然科学基金;
关键词：
CONSTRUCTION; CYCLIZATION; HETEROCYCLES; DERIVATIVES; ALDEHYDES; CASCADE; ALKENES; ROUTE; MODE; ARYL;
D O I：
10.1021/acs.orglett.2c02072
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Lewis-base-catalyzed three-component electrophilic thiofunctionalization of cyclopropene with phenol is developed to furnish various trisubstituted chromanes in high trans-diasteroselectivity. This metal-free protocol is easy to scaleup, offers a unique 2,2,3-substitution pattern, and delivers chromanes with diversified core substitution patterns. The unprecedented tolerance of strong electron-withdrawing substituents at the phenol renders the protocol indispensable to access the otherwise inaccessible chromane chemical space that is important for medicinal chemistry campaigns.
引用
收藏
页码：5693 / 5697
页数：5
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