Copper-Catalyzed Synthesis of 2, 4-Disubstituted Allenoates from α-Diazoesters

被引：88
作者：
Hassink, Matthew [1 ]
Liu, Xiaozhong [1 ]
Fox, Joseph M. [1 ]
机构：
[1] Univ Delaware, Brown Labs, Dept Chem & Biochem, Newark, DE 19716 USA
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 09期
基金：
美国国家科学基金会;
关键词：
ALLENIC ESTERS; ENANTIOSELECTIVE SYNTHESIS; BICYCLIC; 6-ALKOXY-2-PYRONES; REGIOSPECIFIC SYNTHESIS; 4+2 ANNULATION; REARRANGEMENT; SULFIDES; ALLENECARBOXYLATES; ISOMERIZATION; ACCELERATION;
D O I：
10.1021/ol2006242
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cu-catalyzed method for coupling alpha-substituted-alpha-diazoesters with terminal alkynes to give substituted allenoates is described. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.
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收藏
页码：2388 / 2391
页数：4
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