Diastereoselective Reductions of β-Keto Sulfoximines

Article abstract of DOI:10.1021/jo00346a011

(S)-β-Keto sulfoximines have been prepared by butyllithium-mediated condensation of (+)-(S)-N,S-dimethyl-S-phenylsulfoximine with nitriles.The β-keto sulfoximines on treatment with a variety of reducing agents afforded β-hydroxy sulfoximines with varying diastereomeric ratios.Highest asymmetric inductions were observed with gaseous diborane.A sulfoximine-borane complex is suggested as an intermediate.Raney nickel desulfurization of the β-hydroxy sulfoximines afforded secondary alcohols with optical purities in the 18-69percent range.