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

DOI: 10.1021/jo00391a049

Source and publish data:

Journal of Organic Chemistry p. 3435 - 3441 (1987)

Update date:2022-08-03

Topics:

Authors:

Hwang, Ki-Jun

Logusch, Eugene W.

Brannigan, Lawrence H.

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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.

Full text of DOI:10.1021/jo00391a049

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