Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction

Florent Huguenot; Thierry Brigaud

doi:10.1021/jo0607717

Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction

J Org Chem. 2006 Sep 1;71(18):7075-8. doi: 10.1021/jo0607717.

Authors

Florent Huguenot¹, Thierry Brigaud

Affiliation

¹ Laboratoire Réactions Sélectives et Applications, UMR CNRS 6519, Université de Reims-Champagne-Ardenne, Faculté des Sciences, BP 1039, 51687 Reims Cedex 2, France.

PMID: 16930068
DOI: 10.1021/jo0607717

Abstract

Diastereomerically pure alpha-trifluoromethyl alpha-amino nitriles obtained by Strecker-type reactions from chiral CF3 imines and iminium proved to be very attractive versatile intermediates for the synthesis of various alpha-trifluoromethyl amino compounds. From these synthons, both enantiomers of alpha-trifluoromethyl alanine, trifluoromethyl 1,2-diamines, and amino alcohols were conveniently obtained in enantiopure form in high yields in a few steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alanine / analogs & derivatives*
Alanine / chemical synthesis
Alanine / chemistry
Amino Alcohols / chemical synthesis*
Amino Alcohols / chemistry
Amino Alcohols / isolation & purification
Catalysis
Chemistry, Organic / methods*
Diamines / chemical synthesis*
Diamines / chemistry
Diamines / isolation & purification
Imines / chemistry
Stereoisomerism

Substances

Amino Alcohols
Diamines
Imines
alpha-trifluoromethylalanine
Alanine