Organocatalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β,γ-Unsaturated α-Ketoesters: An Access to Chiral Indolin-3-ones with Two Adjacent Tertiary Stereogenic Centers

被引：22

作者：

Chen, Shanren ^{[1
]}

Wang, Youming ^{[1
]}

Zhou, Zhenghong ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Inst & State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; 1ST TOTAL-SYNTHESIS; 2-MONOSUBSTITUTED INDOLIN-3-ONES; STEREOCONTROLLED CONSTRUCTION; 2-SUBSTITUTED INDOLIN-3-ONES; ENANTIOSELECTIVE SYNTHESIS; INDOLE ALKALOIDS; MANNICH REACTION; DUOCARMYCIN-A; CATALYSIS;

D O I：

10.1021/acs.joc.6b02070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Michael addition of 1-acetylindolin-3-ones to beta,gamma-unsaturated a-keto esters was investigated for the synthesis of chiral indolin-3-ones with two adjacent tertiary stereogenic centers. Under the catalysis of a chiral bifunctional squaramide derived from L-tert-leucine, a wide range of 1-acetylindolin-3-ones and beta,gamma-unsaturated alpha-ketoesters were well-tolerated in this transformation to provide the corresponding novel densely functionalized chiral indolin-3-one derivatives in high yield with excellent diastereo- and enantioselectivity under mild reaction conditions.

引用

页码：11432 / 11438

页数：7

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