Asymmetric [3+2] cycloaddition of donor-acceptor cyclopropanes with azadienes enabled by Brønsted base catalysis

被引：3

作者：

Li, Shu ^{[1
]}

Dong, Zhi-Hong ^{[1
]}

Dan, Si-Yu ^{[1
]}

Zheng, Mei-Jun ^{[1
]}

Long, Teng ^{[1
]}

Zhan, Jie ^{[1
]}

Zhou, Qing ^{[1
]}

Chu, Wen-Dao ^{[1
]}

Liu, Quan-Zhong ^{[1
]}

机构：

[1] China West Normal Univ, Coll Chem & Chem Engn, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 10期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ACID; CONSTRUCTION; ANNULATION; VINYLCYCLOPROPANES; HETEROCYCLES; DERIVATIVES; ACTIVATION; REACTIVITY; DIASTEREO;

D O I：

10.1039/d4qo00002a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral bifunctional Bronsted base-catalyzed enantioselective [3 + 2] cycloaddition of D-A cyclopropanes and azadienes is reported. A wide range of spiro-cyclopentane benzofurans bearing three contiguous stereogenic centers are obtained in excellent yields (up to 97%), moderate to excellent enantioselectivities (up to 95%) and moderate diastereoselectivities. The protocol features broad substrate scope, mild reaction conditions and high functional group tolerance. A chiral bifunctional Bronsted base-catalyzed enantioselective [3 + 2] cycloaddition of D-A cyclopropanes and azadienes is reported. The protocol features broad substrate scope, mild reaction conditions and high functional group tolerance.

引用

页码：2905 / 2910

页数：6

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