Jump to main content
Jump to site search


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

Author affiliations

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

Back to tab navigation

Supplementary files

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, Advance Article

  •   Request permissions

    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, Advance Article , DOI: 10.1039/C9OB02241D

Search articles by author

Spotlight

Advertisements