Gaining Absolute Control of the Regiochemistry in the Cobalt-Catalyzed 1,4-Hydrovinylation Reaction

被引：64

作者：

Arndt, Marion ^{[1
]}

Dindaroglu, Mehmet ^{[2
]}

Schmalz, Hans-Guenther ^{[2
]}

Hilt, Gerhard ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

[2] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 23期

关键词：

COBALT(I)-CATALYZED DIELS-ALDER; PROPARGYLIC PHOSPHONIUM SALTS; PARALLEL KINETIC RESOLUTION; PHOSPHINE-PHOSPHITE-LIGANDS; BIDENTATE CHELATE LIGANDS; ASYMMETRIC HYDROVINYLATION; 1,3-DIENES; REGIOSELECTIVITY; 1,4-ADDITION; DIENOPHILES;

D O I：

10.1021/ol202696n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates the corresponding linear product in both excellent yields and regioselectivities. The catalyst system exhibits a high tolerance toward functional groups, and the very mild reaction conditions allow the synthesis of 1,4-dienes without isomerization into conjugated systems.

引用

页码：6236 / 6239

页数：4

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