Oxidative [2+1+1+1] Annulation of Aldehydes and Methylene Nitriles: Synthesis of Diastereoselective Polysubstituted Cyclopentenes

被引：1

作者：

Gao, Na ^{[1
]}

Liu, Xiaoyu ^{[1
]}

Yuan, Xu ^{[1
]}

Hu, Bingwei ^{[1
]}

Jiang, Peiyun ^{[1
]}

Lin, Jun ^{[1
]}

Jin, Yi ^{[1
]}

机构：

[1] Yunnan Univ, Key Lab Med Chem Nat Resource, Yunnan Prov Ctr Res & Dev Nat Prod, Sch Chem Sci & Technol,Minist Educ, Kunming 650091, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 15期

关键词：

DERIVATIVES; STEREOCHEMISTRY; CYCLIZATION;

D O I：

10.1021/acs.joc.2c01330

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a green cascade approach to prepare a variety of diastereoselective polysubstituted cyclopentene derivatives through metal-free oxidative [2 + 1 + 1 + 1] annulation of aldehydes and methylene nitriles. Mechanistic studies demonstrated that the reaction underwent a four-step cascade reaction including air oxidation and Michael addition to obtain the final product. This reaction features readily available starting materials, transition metal-free, eco-friendly operations, gram-scale syntheses, and wide functional group tolerance. The methodology may be useful for the construction of polysubstituted cyano-cyclopentene heterocycles with potential biological activity.

引用

页码：10298 / 10308

页数：11

共 28 条

[21] Phosphine-catalyzed [3+2] annulation of α-substituted allenoates with ester-activated α,β-unsaturated imines: a novel variation of the Lu [3+2] cycloaddition reaction [J].