Asymmetric synthesis of fluorinated amino macrolactones through ring-closing metathesis.
The synthesis of new chiral fluorinated amino and azamacrolactones of types 1 and 2 is described. A ring-closing metathesis (RCM) reaction constitutes the key step in this methodology, which uses fluorinated amino alcohols 7 as starting materials. The influence of the CF2 group, which is located in the alpha-position relative to the carbon bearing the amino group, on the efficiency of the RCM reaction is noteworthy. This method allows for the preparation of the desired fluorinated macrolactones in excellent yields.
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100, Burjassot, Spain. santos.fustero@uv.es
Fernández
Begoña
B
Sanz-Cervera
Juan F
JF
Mateu
Natalia
N
Mosulén
Silvia
S
Carbajo
Rodrigo J
RJ
Pineda-Lucena
Antonio
A
Ramírez de Arellano
Carmen
C
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000605:Amino Alcohols; D006845:Hydrocarbons, Fluorinated; D007783:Lactones; D047028:Macrocyclic Compounds