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Issue 46, 2019
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N-Isopropylsulfinylimines vs. N-tert-butylsulfinylimines in the stereoselective synthesis of sterically hindered amines: an improved synthesis of enantiopure (R)- and (S)-rimantadine and the trifluoromethylated analogues

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Abstract

An improved fully stereoselective synthesis of both enantiomers of rimantadine and its trifluoromethylated analogues has been developed, using N-isopropylsulfinylimines as a starting chiral material, proving the superiority of the isopropyl group as a chiral inducer over the tert-butyl group in the case of hindered N-sulfinylimines.

Graphical abstract: N-Isopropylsulfinylimines vs. N-tert-butylsulfinylimines in the stereoselective synthesis of sterically hindered amines: an improved synthesis of enantiopure (R)- and (S)-rimantadine and the trifluoromethylated analogues

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Article information


Submitted
16 Oct 2019
Accepted
03 Nov 2019
First published
04 Nov 2019

Org. Biomol. Chem., 2019,17, 9854-9858
Article type
Communication

N-Isopropylsulfinylimines vs. N-tert-butylsulfinylimines in the stereoselective synthesis of sterically hindered amines: an improved synthesis of enantiopure (R)- and (S)-rimantadine and the trifluoromethylated analogues

N. Moreno, R. Recio, V. Valdivia, N. Khiar and I. Fernández, Org. Biomol. Chem., 2019, 17, 9854
DOI: 10.1039/C9OB02241D

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