N-Isopropylsulfinyliminesvs. 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:
Affiliation:
1. Departamento de Química Orgánica y Farmacéutica
2. Facultad de Farmacia
3. Universidad de Sevilla
4. Sevilla
5. Spain
6. Instituto de Investigaciones Químicas
7. CSIC-Universidad de Sevilla
Abstract
In contrast toN-tert-butylsulfinylimines, the use ofN-isopropylsulfinylimines as starting chiral material allows the stereoselective synthesis of both enantiomers of rimantadine and its trifluoromethylated analogues.
Funder
Ministerio de Economía y Competitividad
Ministerio de Ciencia, Innovación y Universidades
Publisher
Royal Society of Chemistry (RSC)
Subject
Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry
Link
http://pubs.rsc.org/en/content/articlepdf/2019/OB/C9OB02241D
Reference55 articles.
1. Additions of Organometallic Reagents to CN Bonds: Reactivity and Selectivity
2. Asymmetric, Catalytic Phenyl Transfer to Imines: Highly Enantioselective Synthesis of Diarylmethylamines
3. Chiral non-racemic sulfinimines: versatile reagents for asymmetric synthesis
4. Asymmetric synthesis of amino acids using sulfinimines (thiooxime S-oxides)
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1. Organosulfur Compounds as Chiral Building Blocks;Chiral Building Blocks in Asymmetric Synthesis;2022-08-12
2. Application of Chiral Sulfinamides into Formation and Reduction of Sulfinylketimines to Obtain Valuable α‐Chiral Primary Amines;European Journal of Organic Chemistry;2020-07-17
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