2-Methyl-2-propanyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate
CAS Number:
154026-93-4
Molecular Formula:
C10H19ClO4
Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles
Literature Information
Publication Date
2020-04-17
DOI
10.1039/D0QO00348D
Impact Factor
5.281
Authors
Luyao Li, Bo Zhu, Huihui Fan, Zhiyong Jiang, Junbiao Chang
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure](https://static.chemtradehub.com/structs/480/480452-37-7-0898.webp "N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure")
N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide
CAS Number:
480452-37-7
Molecular Formula:
C16H22ClN5O3
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