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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.

Abstract

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

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Publication details

The article was received on 16 Oct 2019, accepted on 03 Nov 2019 and first published on 04 Nov 2019


Article type: Communication
DOI: 10.1039/C9OB02241D
Org. Biomol. Chem., 2019, Accepted Manuscript

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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.

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

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