Diastereoselective synthesis of fluorinated, seven-membered beta-amino acid derivatives via ring-closing metathesis.
[reaction: see text] Cis and trans seven-membered gamma,gamma-difluorinated beta-amino acid derivatives (III) have been prepared with a sequence that starts with imidoyl halides (I), which are condensed with suitable ester enolates to give intermediates (II). These, in turn, can be cyclized by means of a ring-closing olefin metathesis reaction and the product stereoselectively reduced to yield compounds (III) in good overall yields.
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Bartolomé
Ana
A
Sanz-Cervera
Juan F
JF
Sánchez-Roselló
María
M
arcía Soler
Juan
J
Ramírez de Arellano
Carmen
C
Fuentes
Antonio Simón
AS
D000596:Amino Acids / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D005461:Fluorine