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Issue 5, 2016
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Gold-catalyzed three-component spirocyclization: a one-pot approach to functionalized pyrazolidines

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Abstract

An efficient, highly atom economic synthesis of hitherto unknown spirocyclic pyrazolidines in a one-pot process was developed. The gold-catalyzed three-component coupling of alkynols, hydrazines and aldehydes or ketones likely proceeds via cycloisomerization of the alkynol to an exocyclic enol ether and subsequent [3 + 2]-cycloaddition of an azomethine ylide. A library of 29 derivatives with a wide range of functional groups was synthesized in up to 97% yield. With this new method, every position in the final product can be substituted which renders the method ideal for applications in combinatorial or medicinal chemistry.

Graphical abstract: Gold-catalyzed three-component spirocyclization: a one-pot approach to functionalized pyrazolidines

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Supplementary files

Article information


Submitted
30 Nov 2015
Accepted
15 Dec 2015
First published
15 Dec 2015

This article is Open Access

Org. Biomol. Chem., 2016,14, 1579-1583
Article type
Paper

Gold-catalyzed three-component spirocyclization: a one-pot approach to functionalized pyrazolidines

B. Wagner, W. Hiller, H. Ohno and N. Krause, Org. Biomol. Chem., 2016, 14, 1579
DOI: 10.1039/C5OB02453F

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