Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita-Baylis-Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO

被引：56

作者：

Arupula, Sanjeeva K. ^{[1
]}

Guin, Soumitra ^{[1
]}

Yadav, Anubha ^{[1
]}

Mobin, Shaikh M. ^{[1
]}

Samanta, Sampak ^{[1
]}

机构：

[1] Indian Inst Technol Indore, Discipline Chem, Indore 453552, Madhya Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 05期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; HIGHLY REGIOSELECTIVE SYNTHESIS; 3,3'-DISUBSTITUTED OXINDOLES; ENANTIOSELECTIVE SYNTHESIS; 3+2 ANNULATIONS; DOMINO REACTION; 3-SUBSTITUTED OXINDOLES; ACTIVATED ALKENES; MICHAEL ADDITION; RAPID ACCESS;

D O I：

10.1021/acs.joc.7b03090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, organocatalytic, and ecofriendly method has been developed for the quick construction of a wide array of 3,3-disubstituted oxindoles in good to excellent yields and diastereomeric ratio (up to <= 96:4) with excellent functional group tolerance via an allylic alkylation reaction of cyclic sulfamidate imines with a number of MBH carbonates of isatins in 2-MeTHF as an environmentally benign solvent at room temperature using 5 mol % of DABCO. Furthermore, a metal-free-based one-shot synthesis of a medicinally promising polycyclic spirooxindole with an all-carbon spirocenter has been achieved with outstanding dr value (up to <= 99:1).

引用

页码：2660 / 2675

页数：16

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