Diastereoselective 1,2-Addition of Lithiated N-(Trialkylsilyl)methylphenylsulfoximines to Aldehydes: Preparation of 1,4,3-Oxathiazin-2(6H)-one 4-Oxides as Novel Cyclic Sulfoximines

Article abstract of DOI:10.1021/jo00391a049

High field NMR and X-ray crystallographic methods were used to elucidate the diastereoselectivity of 1,2-addition of lithiated N-(trialkylsilyl)methylphenylsulfoximines to aldehydes.The resulting (β-hydroxyalkyl)sulfoximines were readily cyclized with phosgene to yield the novel sulfoximine-derived 1,4,3-oxathiazin-2(6H)-one 4-oxides.