Phosphine-Catalyzed [3+2] Annulation of Hepta-2,3,5-trienedioates with Alkenes for the Construction of Exocyclic Olefinic Cyclopentenes

被引：5

作者：

Li, Dongqiu ^{[1
,2
]}

Zhang, Xiaoqian ^{[1
,2
]}

Han, Wendan ^{[1
,2
]}

Jiao, Jiao ^{[1
,2
]}

Tang, Yuhai ^{[1
,2
]}

Xu, Silong ^{[1
,2
]}

机构：

[1] Xi An Jiao Tong Univ, Sch Chem, Minist Educ, Xian 710049, Peoples R China

[2] Xi An Jiao Tong Univ, Engn Res Ctr Energy Storage Mat & Devices, Minist Educ, Xian 710049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 14期

基金：

中国国家自然科学基金;

关键词：

BAYLIS-HILLMAN ACETATES; ENANTIOSELECTIVE SYNTHESIS; SEQUENTIAL ANNULATION; ASYMMETRIC-SYNTHESIS; CYCLOADDITION; ALLENOATES; ACCESS; BASE; 2,3-BUTADIENOATES; SESQUITERPENES;

D O I：

10.1021/acs.joc.3c00550

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hepta-2,3,5-trienedioates 1 have been employedassubstrates to explore Lewis base-catalyzed annulation reactions. Thisleads to the discovery of a phosphine-catalyzed [3+2] annulation of 1 with electron-deficient alkenes for the construction ofexocyclic olefinic cyclopentenes in good yields and moderate E:Z ratios under mild conditions. The annulationis believed to proceed in a tandem [3+2] cyclization and double bondmigration in which the & epsilon;-ester is crucial to both processes.This reaction also showcases a substrate-controlled divergent reactivitycompared to that of a previous report.

引用

页码：10212 / 10222

页数：11

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