Enantioselective Synthesis of 2-Oxindole Spirofused Lactones and Lactams by Heck/Carbonylative Cylization Sequences: Method Development and Applications

被引：109

作者：

Hu, Huaanzi ^{[1
,2
,3
]}

Teng, Fan ^{[1
,2
,3
]}

Liu, Jian ^{[1
,2
]}

Hu, Weiming ^{[1
,2
,3
]}

Luo, Shuang ^{[1
,2
,3
]}

Zhu, Qiang ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, State Key Lab Resp Dis, 190 Kaiyuan Ave, Guangzhou 510530, Guangdong, Peoples R China

[2] Univ Chinese Acad Sci, 19 A Yuquan Rd, Beijing 100049, Peoples R China

[3] Guangzhou Regenerat Med & Hlth Guangdong Lab, Guangzhou 510005, Guangdong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 27期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; heterocycles; natural products; palladium; spiro-compounds; CATALYZED CYCLIZATION-CARBONYLATION; ASYMMETRIC-SYNTHESIS; QUATERNARY STEREOCENTERS; PALLADIUM; OXINDOLES; CONSTRUCTION; HYDROFORMYLATION; COMPLEXES; OLEFINS; ACIDS;

D O I：

10.1002/anie.201904838

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient one-pot assembly of all-carbon spiro-oxindole compounds from non-oxindole-based materials has been developed through a palladium-catalyzed asymmetric Heck/carbonylative lactonization and lactamization sequence. Diversified spirooxindole gamma-and delta-lactones/lactams were accessed in high yields with good to excellent enantioselectivities (up to 99% ee) under mild reaction conditions. The natural product coixspirolactam A was conveniently synthesized by applying the current methodology, and thus its absolute configuration was elucidated for the first time. Asymmetric synthesis of an effective CRTH2 receptor antagonist has also been demonstrated utilizing this method in the key step.

引用

页码：9225 / 9229

页数：5

共 70 条

[1] ASYMMETRIC HYDROFORMYLATION [J].