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Issue 21, 2020
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Organocatalytic synthesis of chiral CF3-containing oxazolidines and 1,2-amino alcohols: asymmetric oxa-1,3-dipolar cycloaddition of trifluoroethylamine-derived azomethine ylides

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Abstract

A catalytic asymmetric oxa-1,3-dipolar cycloaddition of ketones with trifluoroethylamine-derived azomethine ylides has been developed using cinchona-derived bifunctional thiourea catalysts. This protocol provides an efficient methodology for the facile synthesis of chiral CF3-containing oxazolidines with moderate to excellent yields, excellent diastereoselectivities and enantioselectivities (58–98% yields, up to >20 : 1 dr and 98% ee). Remarkably, these oxazolidines could be facilely converted to CF3-containing 1,2-amino alcohols with vicinal stereogenic centers, which is a privileged structural motif in medicinal chemistry.

Graphical abstract: Organocatalytic synthesis of chiral CF3-containing oxazolidines and 1,2-amino alcohols: asymmetric oxa-1,3-dipolar cycloaddition of trifluoroethylamine-derived azomethine ylides

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Article information


Submitted
16 Aug 2020
Accepted
21 Sep 2020
First published
22 Sep 2020

Org. Chem. Front., 2020,7, 3452-3458
Article type
Research Article

Organocatalytic synthesis of chiral CF3-containing oxazolidines and 1,2-amino alcohols: asymmetric oxa-1,3-dipolar cycloaddition of trifluoroethylamine-derived azomethine ylides

W. Zhu, Q. Su, N. Lin, Q. Chen, Z. Zhang, J. Weng and G. Lu, Org. Chem. Front., 2020, 7, 3452
DOI: 10.1039/D0QO00990C

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