Nickel-Catalyzed Cyclizations of Enoates and Chiral Allenes: An Approach to Domoic Acid

被引：7

作者：

ElDouhaibi, Ahmad S. ^{[1
]}

Kassab, Refaie M. ^{[1
]}

Song, Minsoo ^{[1
]}

Montgomery, John ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 23期

关键词：

alkynes; allenes; C-C coupling; cyclization; nickel; EXCITATORY AMINO-ACIDS; 2+2+2 CYCLOADDITION STRATEGY; (-)-ALPHA-KAINIC ACID; (+)-ALPHA-ALLOKAINIC ACID; ALKENE INTRODUCTION; METAL; ALDEHYDES; STEREOCHEMISTRY; REAGENTS; ALKYNES;

D O I：

10.1002/chem.201100444

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Come on allene, taloo-rye-aye! The first examples of nickel-catalyzed enoate/chiral allene cyclization reactions are reported. In the coupling process employing dimethylzinc, densely functionalized pyrrolidines are obtained with stereoselective installation of the C3 and C4 chiral centers and the diene functionality at C4. The process provides rapid access to an advanced intermediate towards the synthesis of domoic acid (see graphic). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6326 / 6329

页数：4

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