NHC-catalyzed oxidative γ-addition of α,β-unsaturated aldehydes to isatins: a high-efficiency synthesis of spirocyclic oxindole-dihydropyranones

被引：43

作者：

Liu, Rui ^{[1
]}

Yu, Chenxia ^{[1
]}

Xiao, Zhaoxin ^{[1
]}

Li, Tuanjie ^{[1
]}

Wang, Xiangshan ^{[1
]}

Xie, Yuanwei ^{[1
]}

Yao, Changsheng ^{[2
]}

机构：

[1] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

[2] Jiangsu Normal Univ, Key Lab Biotechnol Med Plant, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 12期

基金：

中国国家自然科学基金;

关键词：

N-HETEROCYCLIC-CARBENE; ENANTIOSELECTIVE SYNTHESIS; COOPERATIVE CATALYSIS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; STETTER REACTIONS; BENZOIN REACTION; ENALS; ANNULATION; LACTAMS;

D O I：

10.1039/c3ob42008f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This manuscript discloses an efficient construction of the spirocyclic oxindole-dihydropyranone scaffold via the N-heterocyclic carbene (NHC)-catalyzed oxidative gamma-functionalization of alpha,beta-unsaturated aldehydes bearing gamma-H with isatin derivatives. The ready availability of the starting materials, easy work-up, mild reaction conditions and the potential utilization value of the products make this strategy attractive.

引用

页码：1885 / 1891

页数：7

共 63 条

[1] Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences [J].