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Issue 11, 2020
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Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

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Abstract

Herein, we report a chiral bifunctional thiourea catalyzed asymmetric Michael addition reaction between 2-(trifluoromethyl)oxazol-5(2H)-one as a direct C-2-position nucleophile and 4-nitro-5-styrylisoxazoles for the first time. The reaction affords the corresponding products bearing adjacent CF3-substituted hetero-quaternary and tertiary stereocenters in moderate to high yields (up to 94% yield) with good to excellent enantioselectivities (up to 99% ee) and excellent diastereoselectivities (up to >20 : 1 dr) under mild reaction conditions. Moreover, the selected compounds displayed good biological activities and further investigation is underway.

Graphical abstract: Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

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Article information


Submitted
20 Mar 2020
Accepted
15 Apr 2020
First published
17 Apr 2020

Org. Chem. Front., 2020,7, 1343-1348
Article type
Research Article

Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

L. Li, B. Zhu, H. Fan, Z. Jiang and J. Chang, Org. Chem. Front., 2020, 7, 1343
DOI: 10.1039/D0QO00348D

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