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Issue 111, 2015
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Asymmetric synthesis of spiro[chroman-3,3′-pyrazol] scaffolds with an all-carbon quaternary stereocenter via a oxa-Michael–Michael cascade strategy with bifunctional amine-thiourea organocatalysts

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Abstract

An efficient chiral bifunctional amine-thiourea catalysed cascade oxa-Michael–Michael addition of 4-alkenyl pyrazolin-3-ones to (E)-2-(2-nitrovinyl)phenol for the synthesis of chiral heterocyclic systems containing spiro[chroman-3,3′-pyrazol] scaffolds has been developed. This reaction afforded the desired products in high to excellent yields (up to 98%) with moderate to high enantioselectivities (up to 99%) and diastereoselectivities (up to 20 : 1) under low catalyst (15 mol%) concentration. This catalytic asymmetric reaction provides an efficient route toward the synthesis of chiral spiro[chroman-3,3′-pyrazol] derivatives containing three contiguous stereocenters which possess potential pharmaceutical activities.

Graphical abstract: Asymmetric synthesis of spiro[chroman-3,3′-pyrazol] scaffolds with an all-carbon quaternary stereocenter via a oxa-Michael–Michael cascade strategy with bifunctional amine-thiourea organocatalysts

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Supplementary files

Article information


Submitted
02 Sep 2015
Accepted
15 Oct 2015
First published
15 Oct 2015

RSC Adv., 2015,5, 91108-91113
Article type
Communication

Asymmetric synthesis of spiro[chroman-3,3′-pyrazol] scaffolds with an all-carbon quaternary stereocenter via a oxa-Michael–Michael cascade strategy with bifunctional amine-thiourea organocatalysts

W. Zheng, J. Zhang, S. Liu, C. Yu and Z. Miao, RSC Adv., 2015, 5, 91108
DOI: 10.1039/C5RA17792H

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