Derailed Ohira-Bestmann Reaction of γ,δ-Unsaturated Aldehydes for the Stereoselective Synthesis of Cyclopenta[c]pyrazoles

被引：3

作者：

Sandmeier, Tobias ^{[1
]}

Sievertsen, Niels ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Dept Chem & Appl Biosci, Lab Organ Chem, CH-8093 Zurich, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2020年 / 103卷 / 06期

关键词：

pyrazoles; cycloaddition reactions; homologation; domino reactions; cascade reactions; Ohira-Bestmann reaction; CYCLOADDITIONS; CHEMISTRY;

D O I：

10.1002/hlca.202000058

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of cyclopenta[c]pyrazoles from gamma,delta-unsaturated aldehydes by a domino sequence involving one-carbon homologation and intramolecular azomethine imine 1,3-dipolar cycloaddition is disclosed. The fused pyrazoles bearing aromatic and aliphatic substituents are obtained in good yields and excellent diastereomeric purity. Additionally, the synthetic utility of the pyrazole products generated by this method has been highlighted in a series of functionalization reactions. The method presented opens strategic opportunities for the synthesis of pyrazole-containing biologically active compounds.

引用

页数：5

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