NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates

被引：42

作者：

Li, Sha ^{[1
]}

Tang, Ziwei ^{[1
]}

Wang, Yang ^{[2
]}

Wang, Dan ^{[1
]}

Wang, Zhanlin ^{[1
]}

Yu, Chenxia ^{[1
]}

Li, Tuanjie ^{[1
]}

Wei, Donghui ^{[2
]}

Yao, Changsheng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China

[2] Zhengzhou Univ, Coll Chem & Mol Engn, 100 Sci Ave, Zhengzhou 450001, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

基金：

中国国家自然科学基金;

关键词：

N-HETEROCYCLIC CARBENES; ALPHA-ALLENIC ESTERS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; 3+2 CYCLOADDITION; EFFICIENT PREPARATION; KETENES; GROWTH; 2,3-ALLENOLS; DERIVATIVES;

D O I：

10.1021/acs.orglett.8b04082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-heterocyclic carbene (NHC) catalyzed gamma-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the gamma-adduct was more energetically favorable than that of the alpha-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.

引用

页码：1306 / 1310

页数：5

共 9 条

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