Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition

被引：58

作者：

Jenkins, Aireal D. ^{[1
]}

Herath, Ananda ^{[1
]}

Song, Minsoo ^{[1
]}

Montgomery, John ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 36期

基金：

美国国家科学基金会;

关键词：

FACILE CONSTRUCTION; CYCLIZATION; ALLENES; ALKENES; ALKYNES; ESTERS; ENONES; INTERMEDIATE; ANNULATIONS; DERIVATIVES;

D O I：

10.1021/ja206722t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Strategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal-alkyne cycloaddition directly affords cyclopentenols, whereas the enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of these processes likely involves formation and protonation of a metallacyclic intermediate. The general strategy provides a straightforward entry to five-membered ring products from simple, stable pi-systems.

引用

页码：14460 / 14466

页数：7

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