Highly enantioselective synthesis of fluorinated gamma-amino alcohols through proline-catalyzed cross-Mannich reaction.
A new, simple route for the synthesis of fluorinated beta-alkyl gamma-amino alcohols in optically pure form in only two steps and featuring proline catalysis from inexpensive and readily available starting materials is described. The applied strategy allows for the introduction of diversity into both the beta-fluoroalkyl and alpha-alkyl groups of these compounds. [reaction: see text]
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain.
Jiménez
Diego
D
Sanz-Cervera
Juan F
JF
Sánchez-Roselló
María
M
Esteban
Elisabet
E
Simón-Fuentes
Antonio
A
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D006845:Hydrocarbons, Fluorinated; D008352:Mannich Bases; D011392:Proline