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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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Supplementary files

Article information


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

Org. Chem. Front., 2020, Advance Article
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, Advance Article , DOI: 10.1039/D0QO00990C

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