Nickel-catalyzed reductive coupling of alkynes and epoxides

被引：115

作者：

Molinaro, C ^{[1
]}

Jamison, TF ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 27期

关键词：

D O I：

10.1021/ja0361401

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-π-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane. Copyright © 2003 American Chemical Society.

引用

页码：8076 / 8077

页数：2

共 49 条

[41] STRUCTURE AND MECHANISM OF FORMATION OF METALLOOXACYCLOBUTANE COMPLEX PT[C2(CN)4O][AS(C6H5)3]2, PRODUCT OF REACTION BETWEEN TETRACYANOOXIRANE AND PT[AS(C6H5)3]4 [J].