Phosphine-Catalyzed Annulation Reactions of 2-Butynoate and α-Keto Esters: Synthesis of Cyclopentene Derivatives

被引：34
|
作者：
Mbofana, Curren T. [1 ]
Miller, Scott J. [1 ]
机构：
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源：
ACS CATALYSIS | 2014年 / 4卷 / 10期
基金：
美国国家科学基金会;
关键词：
alkynoates; alpha-keto esters; phosphines; organocatalysis; annulation reactions; fused rings; C-C bond cleavage; 3+2 CYCLOADDITION; ALLENOATE ADDITIONS; CYANIDE ION; IMINES; ALKENES; 2,3-BUTADIENOATES; TRIBUTYLPHOSPHINE; ORGANOCATALYSIS; PRECURSORS; DIVERSITY;
D O I：
10.1021/cs501117h
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
We have developed phosphine-catalyzed annulation reactions for the synthesis of highly substituted cyclopentene derivatives from 2-alkynoate and alpha-keto esters. These transformations involve carbon carbon bond cleavage of alpha-keto esters. Preliminary mechanistic studies suggest that, in addition to facilitating carbon carbon bond formation, the phosphine catalyst plays a role in promoting methanolysis.
引用
收藏
页码：3671 / 3674
页数：4
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