Organocatalytic asymmetric synthesis of trans-configured trispirooxindoles through a cascade Michael-cyclization reaction

被引：13

作者：

Wu, Chaoling ^{[1
]}

Jing, Linhai ^{[1
]}

Qin, Dabin ^{[1
]}

Yin, Mingxing ^{[1
]}

He, Qiuzuo ^{[1
]}

机构：

[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 26期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; Trispirooxindole; 3-Isothiocyanato oxindole; Michael-cyclization reaction; Cascade reaction; DOMINO MICHAEL/CYCLIZATION REACTION; AMINO-THIOCARBAMATE CATALYSTS; AZA-HENRY REACTION; 3-ISOTHIOCYANATO OXINDOLES; ENANTIOSELECTIVE SYNTHESIS; HIGHLY EFFICIENT; THIOUREA CATALYSTS; BIFUNCTIONAL ORGANOCATALYSTS; POLYCYCLIC SPIROOXINDOLES; ISOTHIOCYANATO OXINDOLES;

D O I：

10.1016/j.tetlet.2016.05.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient stereoselective Michael-cyclization reaction of 3-isothiocyanato oxindoles to cyclic methyleneindolinones has been described. The protocol provides a facile and efficient access to chiral trans-configured trispirooxindoles containing two quaternary stereocenters in good yields (up to 89%) with good diastereoselectivities (up to 90:10) and high enantioselectivities (up to 94% ee) under mild conditions. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2857 / 2860

页数：4

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