Enantioselective Synthesis of Cyclopentanes by Phosphine-Catalyzed β,γ-Annulation of Allenoates

被引：1

作者：

Zhang, Chenxi ^{[1
]}

Maddigan-Wyatt, Jeremy T. ^{[1
]}

Nguyen, Xuan ^{[1
]}

Seitz, Antonia ^{[1
]}

Breugst, Martin ^{[2
]}

Lupton, David W. ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[2] Tech Univ Chemnitz, Inst Chem, D-09111 Chemnitz, Germany

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 37期

基金：

澳大利亚研究理事会;

关键词：

ELECTRON-DEFICIENT OLEFINS; 3+2 CYCLOADDITION; DOMINO REACTION; ANNULATIONS; ALLENES; 2,3-BUTADIENOATES; DERIVATIVES; MALEIMIDES; UMPOLUNG;

D O I：

10.1021/acs.orglett.4c02371

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the enantioselective phosphine-catalyzed beta,gamma-annulation of electron-poor allenes with bifunctional malonates. The reaction exploits a 2C phosphonium synthon that when accessed using (R)-SITCP gives 23 cyclopentanes with high stereoselectivity (most >95:5 er and >9:1 dr) and yield. In addition to the (3+2) annulation, a one-pot three-component variant to give the same cyclopentanes and a (3+2) annulation/Dieckmann cyclization cascade, along with mechanistic studies, are reported.

引用

页码：7800 / 7804

页数：5

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