Tertiary Amine-Catalyzed Difluoromethylthiolation of Morita-Baylis-Hillman Carbonates of Isatins with Zard's Trifluoromethylthiolation Reagent

被引：40

作者：

Fan, Xing ^{[1
]}

Yang, Haibin ^{[1
]}

Shi, Min ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Lu, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 01期

基金：

中国国家自然科学基金;

关键词：

3+2] annulation; difluoromethylthiolation; Morita-Baylis-Hillman (MBH) carbonates; organocatalysis; spirocyclic oxindoles; COPPER-MEDIATED TRIFLUOROMETHYLTHIOLATION; ASYMMETRIC 3+2 ANNULATIONS; MODIFIED ALLYLIC COMPOUNDS; ALPHA-FLUORINATED ETHERS; NUCLEOPHILIC TRIFLUOROMETHYLTHIOLATION; ENANTIOSELECTIVE METHODOLOGIES; SPIROCYCLIC OXINDOLES; CONSTRUCTION; ARYL; DIFLUOROMETHYLATION;

D O I：

10.1002/adsc.201600954

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

In this paper, we report that a novel tertiary amine-catalyzed [3+2] annulation between Morita-Baylis-Hillman (MBH) carbonates derived from isatins with thiocarbonyl fluoride (F2C=S) in situ generated from Zard's reagent proceeds smoothly under mild conditions, affording difluoro-methylthiolated spirocyclic oxindoles in good to excellent yields. Moreover, the asymmetric variant could be realized with a modified Cinchona alkaloid, giving the desired cyclic adducts in good to excellent yields with good enantioselectivities.

引用

页码：49 / 57

页数：9

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