Phosphine-catalyzed asymmetric additions of malonate esters to γ-substituted allenoates and allenamides

被引：87

作者：

Sinisi, Riccardo ^{[1
]}

Sun, Jianwei ^{[1
]}

Fu, Gregory C. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2010年 / 107卷 / 48期

基金：

美国国家卫生研究院;

关键词：

allene; catalysis; ALLENES; TRIPHENYLPHOSPHINE; NUCLEOPHILES; 2-ALKYNOATES; DERIVATIVES; ANNULATION; UMPOLUNG;

D O I：

10.1073/pnas.1003597107

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Because carbonyl groups are ubiquitous in organic chemistry, the ability to synthesize functionalized carbonyl compounds, particularly enantioselectively, is an important objective. We have developed a straightforward and versatile method for catalytic asymmetric carbon-carbon bond formation at the gamma-position of carbonyl compounds, specifically, phosphine-catalyzed additions of malonate esters to gamma-substituted allenoates and allenamides. Mechanistic studies have provided insight into the reaction pathway.

引用

收藏

页码：20652 / 20654

页数：3

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