Novel approach for asymmetric synthesis of fluorinated beta-amino sulfones and allylic amines.
[reaction: see text] Enantiomerically pure gamma-fluoroalkyl beta-amino sulfones are readily synthesized in three steps starting from fluorinated imidoyl chlorides and arylmethyl sulfones. A complementary two-step sequence starting from chiral fluorinated beta-amino sulfoxides has also been developed. To illustrate the application of this procedure, a new method for the synthesis of alpha-fluoroalkyl allylic amines in optically pure form involving a Julia methylenation-desulfonylation reaction is presented.
Fustero
Santos
S
Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Soler
Juan García
JG
Bartolomé
Ana
A
Roselló
María Sánchez
MS
D000498:Allyl Compounds / Q000138:chemical synthesis*; D000588:Amines / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis*
D000498:Allyl Compounds; D000588:Amines; D006845:Hydrocarbons, Fluorinated; D013450:Sulfones