Enantioselective Assembly of Spirocyclic Oxindole-dihydropyranones through NHC-Catalyzed Cascade Reaction of Isatins with N-Hydroxybenzotriazole Esters of α,β-Unsaturated Carboxylic Acid

被引：62

作者：

Que, Yonglei ^{[1
]}

Li, Tuanjie ^{[1
]}

Yu, Chenxia ^{[1
]}

Wang, Xiang-Shan ^{[1
]}

Yao, Changsheng ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 06期

基金：

中国国家自然科学基金;

关键词：

HETEROCYCLIC CARBENE CATALYSIS; ASYMMETRIC TOTAL-SYNTHESIS; OXIDATIVE GAMMA-ADDITION; HMG-COA REDUCTASE; STEREOSELECTIVE-SYNTHESIS; ACYL CHLORIDES; ALDEHYDES; SPIROTRYPROSTATIN; SPIROOXINDOLES; 3-ALKYLENYLOXINDOLES;

D O I：

10.1021/jo502920w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An NHC-catalyzed formal [4 + 2] reaction of isatins with N-hydroxybenzotriazole ester of alpha,beta-unsaturated carboxylic acids bearing gamma-H to construct spirocyclic oxindole-dihydropyranones featuring a chiral tetrasubstituted carbon stereogenic center was developed. The high enantioselectivity, the ready availability of the raw materials, the facile assembly, and the potential biological significance of the final products make this protocol an attractive alternative for the synthesis of spirocyclic heterocycles.

引用

页码：3289 / 3294

页数：6

共 4 条

[1] NHC-catalyzed oxidative γ-addition of α,β-unsaturated aldehydes to isatins: a high-efficiency synthesis of spirocyclic oxindole-dihydropyranones
Liu, Rui
Yu, Chenxia
Xiao, Zhaoxin
Li, Tuanjie
Wang, Xiangshan
Xie, Yuanwei
Yao, Changsheng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (12) : 1885 - 1891
[2] N-Heterocyclic carbene-catalyzed [4+2] cyclization of α, β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole-dihydropyranones
Zhu, Ling
Yu, Chenxia
Li, Tuanjie
Wang, Yuhong
Lu, Yinan
Wang, Wenjing
Yao, Changsheng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (04) : 1485 - 1491
[3] N-Heterocyclic-Carbene-Catalyzed Reaction of α-Bromo-α,β-Unsaturated Aldehyde or α,β-Dibromoaldehyde with Isatins: An Efficient Synthesis of Spirocyclic Oxindole-Dihydropyranones
Yao, Changsheng
Xiao, Zhaoxin
Liu, Rui
Li, Tuanjie
Jiao, Weihui
Yu, Chenxia
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (02) : 455 - 458
[4] Direct enantioselective vinylogous aldol-cyclization cascade reaction of allyl pyrazoleamides with isatins: asymmetric construction of spirocyclic oxindole-dihydropyranones
Li, Tian-Ze
Jiang, Yu
Guan, Yu-Qing
Sha, Feng
Wu, Xin-Yan
CHEMICAL COMMUNICATIONS, 2014, 50 (74) : 10790 - 10792

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