Issue 85, 2018

Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles

Abstract

A copper-catalyzed asymmetric propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones as C,O-bisnucleophiles through the desilylation-activated strategy has been developed. With the catalysis of Cu(OAc)2·H2O in combination with a chiral tridentate P,N,N-ligand, the reaction displayed a broad substrate scope, and thus provided a variety of chiral dihydropyrano[2,3-c]pyrazoles in high yields and with excellent enantioselectivities (up to 96% ee).

Graphical abstract: Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles

Supplementary files

Article information

Article type
Communication
Submitted
14 Jul 2018
Accepted
28 Sep 2018
First published
29 Sep 2018

Chem. Commun., 2018,54, 12033-12036

Copper-catalyzed propargylic [3+3] cycloaddition with 1H-pyrazol-5(4H)-ones: enantioselective access to optically active dihydropyrano[2,3-c]pyrazoles

L. Li, Z. Liu and X. Hu, Chem. Commun., 2018, 54, 12033 DOI: 10.1039/C8CC05706K

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