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
收藏
页码：11432 / 11438
页数：7
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