Asymmetric [4+2] cycloaddition of azlactones with dipolar copper-allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives

被引：21

作者：

Sun, Bing-Bing ^{[1
]}

Hu, Qing-Xian ^{[1
]}

Hu, Jia-Ming ^{[1
]}

Yu, Jie-Qiang ^{[1
]}

Jia, Jun ^{[2
]}

Wang, Xing-Wang ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Soochow Univ, Anal & Testing Ctr, Suzhou 215123, Peoples R China

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 30期

基金：

中国国家自然科学基金;

关键词：

Asymmetric cycloaddition; Dipolar copper-allenylidene; 3,4-Dihydroquinolin-2-ones; Enolate azlactones; TRANSITION-METAL CATALYSIS; 1,3-DIPOLAR CYCLOADDITION; DEAROMATIZATION; DIVERSITY; ACCESS; CONSTRUCTION; QUINOLINONES; MUNCHNONES; ANNULATION; YLIDES;

D O I：

10.1016/j.tetlet.2019.06.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, a pybox-copper catalyzed enantioselective decarboxylative [4+2] cycloaddition reaction of ethynyl benzoxazinanones with azlactones has been developed, which provides optically active 3,4-dihydroquinolin-2-ones in high yields with good enantioselectivities and diastereoselectivities. In this transformation, the chiral dipolar copper-allenylidene intermediates are kinetically generated via decarboxylative ethynyl benzoxazinanones, followed by the attack of the enolate azlactones to form enantiomerically enriched 3,4-dihydroquinolin-2-one structures. (C) 2019 Published by Elsevier Ltd.

引用

页码：1967 / 1970

页数：4

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