Organocatalytic Regiodivergent Ring Expansion of Cyclobutanones for the Enantioselective Synthesis of Azepino[1,2-a]indoles and Cyclohepta[b]indoles

被引：39
|
作者：
Yang, Wu-Lin [1 ,2 ]
Li, Wen [1 ,2 ]
Yang, Zhong-Tao [1 ,2 ]
Deng, Wei-Ping [1 ,2 ,3 ]
机构：
[1] East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China
[3] Zhejiang Normal Univ, Dept Chem, Minist Educ Adv Catalysis Mat, Key Lab, Jinhua 321004, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 10期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
AZOMETHINE YLIDES; MICHAEL ADDITION; 3+3 ANNULATION; INDOLE; DERIVATIVES; CONSTRUCTION; ACCESS; CYCLOADDITION; KETONES; POTENT;
D O I：
10.1021/acs.orglett.0c01406
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regiodivergent organocatalytic enantioselective Michael addition/three-atom ring expansion sequence of electron-withdrawing group activated cyclobutanones with 2-nitrovinylindoles was developed. A series of azepino[1,2-a]indoles were obtained with exclusive regioselectivities and high diastereo- and enantioselectivities (up to >20:1 dr, 96% ee) with the application of the N1 nucleophilic site of the indole nucleus. Meanwhile, various cyclohepta[b]indoles could be accessed with high enantiopurity (up to 96% ee) through the Michael addition/boron-trifluoride-etherate-promoted indole C-3-attack ring expansion process.
引用
收藏
页码：4026 / 4032
页数：7
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