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-Reference-Cited by-同舟云学术

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

Published:2019 Issue:46 Volume:17 Page:9854-9858
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Moreno Nazaret¹²³⁴⁵^ORCID,Recio Rocío¹²³⁴⁵^ORCID,Valdivia Victoria¹²³⁴⁵^ORCID,Khiar Noureddine⁶⁷⁴⁵^ORCID,Fernández Inmaculada¹²³⁴⁵^ORCID

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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