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Synthesis of Trisubstituted Chromanes by Lewis-Base-Catalyzed Three-Component Electrophilic Thiofunctionalization of Cyclopropene with Phenols via a Formal [3 + 3] Annulation
Organic Letters ( IF 5.2 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.orglett.2c02072
Bowen Liu 1 , Lei Wang 2 , Yunfei Qin 1 , Xianxiu Xu 2 , Jinbo Zhao 1, 3
Affiliation  

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 scale-up, 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.

中文翻译:

路易斯碱催化环丙烯与酚通过形式 [3 + 3] 环化的三组分亲电硫代官能化合成三取代色原

开发了一种路易斯碱催化的环丙烯与苯酚的三组分亲电硫代官能化,以提供具有高反式非对映选择性的各种三取代色烷。这种无金属协议易于放大,提供独特的 2,2,3-取代模式,并提供具有多样化核心取代模式的色烷。苯酚处强吸电子取代基的空前耐受性使得该协议对于进入对药物化学活动很重要的其他无法进入的色烷化学空间是必不可少的。
更新日期:2022-08-03
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