Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis.
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.
Fustero
Santos
S
Departamento de Química Organica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Sanchez-Roselló
María
M
Sanz-Cervera
Juan F
JF
Aceña
José Luis
JL
Del Pozo
Carlos
C
Fernandez
Begoña
B
Bartolomé
Ana
A
Asensio
Amparo
A
Ramírez de Arellano
Carmen
C
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry*
D000596:Amino Acids; D005461:Fluorine