Copper-Catalyzed Diastereo- and Enantioselective Decarboxylative [3+2] Cyclization of Alkyne-Substituted Cyclic Carbamates with Azlactones: Access to γ-Butyrolactams Bearing Two Vicinal Tetrasubstituted Carbon Stereocenters

被引：19

作者：

Wang, Ting ^{[1
,2
]}

You, Yong ^{[4
]}

Wang, Zhen-Hua ^{[4
]}

Zhao, Jian-Qiang ^{[4
]}

Zhang, Yan-Ping ^{[4
]}

Yin, Jun-Qing ^{[4
]}

Zhou, Ming-Qiang ^{[3
]}

Cui, Bao-Dong ^{[2
]}

Yuan, Wei-Cheng ^{[4
]}

机构：

[1] Chengdu Univ, Inst Adv Study, Innovat Res Ctr Chiral Drugs, Chengdu 610106, Peoples R China

[2] Zunyi Med Univ, Sch Pharm, Zunyi 563006, Peoples R China

[3] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China

[4] Chengdu Univ, Inst Adv Study, Innovat Res Ctr Chiral Drugs, Chengdu 610106, Peoples R China

来源：

ORGANIC LETTERS | 2023年

关键词：

ASYMMETRIC-SYNTHESIS; LACTAMS; ANNULATION; PRODUCT;

D O I：

10.1021/acs.orglett.3c00075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed diastereo-and enantioselective decar-boxylative [3 + 2] cyclization reaction of alkyne-substituted cyclic carbamates with azlactones has been established. A range of optically pure gamma-butyrolactams bearing two vicinal tetrasubstituted carbon stereo-centers were obtained in high yields with good to excellent stereo-selectivities (up to 99% yield, 99:1 dr, and 99% ee). This is the first example of asymmetric synthesis gamma-butyrolactams containing sterically congested vicinal tetrasubstituted stereocenters via a decarboxylative cyclization pathway.

引用

页码：1274 / 1279

页数：6

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