Remote stereocontrol by sulfinyl groups: reduction of delta-ketosulfoxides.
The reduction of delta-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)3 or L-Selectride as the reducing agents provides delta-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.
García Ruano
José L
JL
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es
Fernández-Ibáñez
M Angeles
MA
Maestro
M Carmen
MC
Rodríguez-Fernández
M Mercedes
MM
D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry*
D007659:Ketones; D013454:Sulfoxides; D013457:Sulfur Compounds