Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes

被引：24

作者：

Amako, Yuka ^{[1
]}

Hori, Hiroto ^{[1
]}

Arai, Shigeru ^{[1
]}

Nishida, Atsushi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 21期

关键词：

PALLADIUM-CATALYZED ADDITION; STEREOSELECTIVE-SYNTHESIS; HYDROGEN-CYANIDE; ALKYNES; CYCLIZATION; CYCLOADDITION; CYANOPALLADATION; ENYNES; STEREOCHEMISTRY; CARBOCYANATION;

D O I：

10.1021/jo401758v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The carbocyanative cyclization of allene-ynes and bis-allenes under nickel catalysis is described. The key steps are the regioselective hydronickelation of allenes and subsequent cyclization via carbometalation. The former step determines the reaction pathway, and the latter controls the stereochemistry of substituted olefins. The products are useful carbo- and heterocycles that include a cyano group, functionalized double bonds, and quaternary carbons.

引用

页码：10763 / 10775

页数：13

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