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Enantioselective Mannich Reaction Promoted by Chiral Phosphinoyl-Aziridines

Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland
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Catalysts 2019, 9(10), 837; https://doi.org/10.3390/catal9100837
Received: 23 September 2019 / Revised: 7 October 2019 / Accepted: 8 October 2019 / Published: 10 October 2019
(This article belongs to the Section Catalysis in Organic and Polymer Chemistry)
In this study, a set of enantiomerically pure aziridines bearing a phosphine oxide moiety were prepared in high yields and tested as chiral catalysts in the direct asymmetric Mannich reaction of hydroxyacetone, an amine (p-anisidine), and various aromatic aldehydes. The appropriate Mannich adducts were formed in chemical yields from moderate to good with a high level of enantio- and diastereoselectivity. The best results were obtained using the catalysts bearing a free NH-aziridine subunit. View Full-Text
Keywords: asymmetric synthesis; aziridines; Mannich reaction; organocatalysis asymmetric synthesis; aziridines; Mannich reaction; organocatalysis
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MDPI and ACS Style

Buchcic, A.; Zawisza, A.; Leśniak, S.; Adamczyk, J.; Pieczonka, A.M.; Rachwalski, M. Enantioselective Mannich Reaction Promoted by Chiral Phosphinoyl-Aziridines. Catalysts 2019, 9, 837.

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