Remote Stereocontrol by Sulfinyl Groups: Reduction of δ-Ketosulfoxides.

The reduction of 5-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 δ-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way. [ABSTRACT FROM AUTHOR]