Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes

被引：94

作者：

Haydl, Alexander M. ^{[1
]}

Xu, Kun ^{[1
]}

Breit, Bernhard ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 24期

关键词：

allenes; allylic compounds; asymmetric catalysis; heterocycles; rhodium; GLUCAGON RECEPTOR ANTAGONIST; INTRAMOLECULAR HYDROAMINATION; INTERMOLECULAR HYDROAMINATION; MICHAEL ADDITION; DERIVATIVES; LIGANDS; ALKYNES; SYSTEM; FUNCTIONALIZATION; HYDROFORMYLATION;

D O I：

10.1002/anie.201501758

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rhodium-catalyzed asymmetric N-selective coupling of pyrazole derivatives with terminal allenes gives access to enantioenriched secondary and tertiary allylic pyrazoles, which can be employed for the synthesis of medicinally important targets. The reaction tolerates a large variety of functional groups and labelling experiments gave insights into the reaction mechanism. This new methodology was further applied in a highly efficient synthesis of JAK 1/2 inhibitor (R)-ruxolitinib.

引用

页码：7149 / 7153

页数：5

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