Crystallization-induced dynamic resolution of Fox chiral auxiliary and application to the diastereoselective electrophilic fluorination of amide enolates

Hodney Lubin; Christophe Dupuis; Julien Pytkowicz; Thierry Brigaud

doi:10.1021/jo400210j

Crystallization-induced dynamic resolution of Fox chiral auxiliary and application to the diastereoselective electrophilic fluorination of amide enolates

J Org Chem. 2013 Apr 5;78(7):3487-92. doi: 10.1021/jo400210j. Epub 2013 Mar 25.

Authors

Hodney Lubin¹, Christophe Dupuis, Julien Pytkowicz, Thierry Brigaud

Affiliation

¹ Laboratoire Synthèse Organique Sélective et Chimie bioOrganique, Université de Cergy-Pontoise, 5 Mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France.

PMID: 23480268
DOI: 10.1021/jo400210j

Abstract

A highly efficient crystallization-induced dynamic resolution (CIDR) of trans-Fox (fluorinated oxazolidine) chiral auxiliary is reported. This chiral auxiliary was used for highly diastereoselective (>98% de) electrophilic fluorination of amide enolates. After removal of the chiral auxiliary, highly valuable enantiopure α-fluorocarboxylic acids and β-fluoroalcohols are obtained.

Publication types

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

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Crystallization
Molecular Structure
Oxazoles / chemistry*
Stereoisomerism
Thermodynamics*

Substances

Amides
Oxazoles
oxazolidine