A new strategy for the synthesis of optically pure beta-fluoroalkyl beta-amino acid derivatives.
The first general approach for the diastereoselective formation of a variety of optically pure anti-beta-fluoroalkyl beta-amino acid derivatives is described. The process relies on the stereocontrolled reaction, mediated by a remote sulfoxide, of fluorinated imines with sulfinylated benzyl carbanions, which are used as synthetic equivalents of chiral ester enolates.
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain.
del Pozo
Carlos
C
Catalán
Silvia
S
Alemán
José
J
Parra
Alejandro
A
Marcos
Vanesa
V
Ruano
José Luis García
JL
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry
D000596:Amino Acids; D006845:Hydrocarbons, Fluorinated; D013454:Sulfoxides