Enantioselective synthesis of fluorinated alpha-amino acids and derivatives in combination with ring-closing metathesis: intramolecular pi-stacking interactions as a source of stereocontrol.
[reaction: see text]. Hydride reduction of C=N bonds stereocontrolled by intramolecular pi-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta-amino alcohols and alpha-amino acid derivatives, respectively.
Fustero
S
S
Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, E-46100 Burjassot, Valencia, Spain. santos.fustero@uv.es
Navarro
A
A
Pina
B
B
Soler
J G
JG
Bartolomé
A
A
Asensio
A
A
Simón
A
A
Bravo
P
P
Fronza
G
G
Volonterio
A
A
Zanda
M
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D005461:Fluorine