Highly diastereoselective synthetic route to enantiopure beta(2)-amino acids and gamma-amino alcohols using a fluorinated oxazolidine (Fox) as chiral auxiliary.
The alkylation reactions of an amide enolate derived from a trifluoromethylated oxazolidine (Fox) chiral auxiliary occur with a complete diastereoselectivity and in good yields with various electrophiles. This reaction provides a versatile and straightforward strategy for the synthesis of beta(2)-amino acids and gamma-amino alcohols in enantiopure form.
Tessier
Arnaud
A
Laboratoire Synthèse Organique Sélective et Chimie Organométallique (SOSCO), UMR CNRS 8123, Université de Cergy-Pontoise, Cergy-Pontoise Cedex, France.
Lahmar
Nour
N
Pytkowicz
Julien
J
Brigaud
Thierry
T
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D000605:Amino Alcohols; D010080:Oxazoles; C064210:oxazolidine