Enantioselective Construction of Vicinal Quaternary- Tetrasubstituted Carbon Stereocenters by Copper-Catalyzed Decarboxylative Propargylic Substitution

被引：22
|
作者：
You, Yong [1 ]
Li, Ting-Ting [2 ]
Sun, Ting-Jia [2 ]
Zhang, Yan-Ping [1 ,3 ]
Wang, Zhen-Hua [1 ]
Zhao, Jian-Qiang [1 ]
Yuan, Wei-Cheng [1 ]
机构：
[1] Chengdu Univ, Inst Adv Study, Innovat Res Ctr Chiral Drugs, Chengdu 610106, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China
[3] Chengdu Univ, Sch Pharm, Chengdu 610106, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 41期
基金：
中国国家自然科学基金;
关键词：
DRUG DISCOVERY; ANNULATION; STRATEGIES;
D O I：
10.1021/acs.orglett.2c03244
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective construction of vicinal tetrasubstituted carbon stereocenters is a formidable challenge in organic synthesis. A copper-catalyzed asymmetric decarboxylative propargylic substitution with 3-amino oxindoles as trisubstituted carbon nucleophiles and propargylic cyclic carbonates as tertiary carbon electrophiles was developed. A range of 3-amino-3,3 & PRIME;-disubstituted oxindoles bearing vicinal quaternary-tetrasubstituted carbon stereo centers were obtained in high yields and good to excellent stereoselectivities (up to 98% yield, > 20:1 dr, and 98.5:1.5 er).
引用
收藏
页码：7671 / 7676
页数：6
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