Diastereoselective 1, 2-addition of lithiated N-(trialkylsilyl) methylphenylsulfoximines to aldehydes: preparation of 1, 4, 3-oxathiazin-2 (6H)-one 4-oxides as novel …

KJ Hwang, EW Logusch, LH Brannigan…

Index: Hwang, Ki-Jun; Logusch, Eugene W.; Brannigan, Lawrence H. Journal of Organic Chemistry, 1987 , vol. 52, # 15 p. 3435 - 3441

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Abstract

The sulfoximine as a functional group was unknown to organic chemistry until 1950, when Bentley and co-workers reported the structure elucidation of methionine sulfoximine, laS2r3 The latter, specifically as the 2S, 5S isomer, is a potent inhibitor of the enzyme glutamine synthetase (EC 6.3. 1.2) 4 and is responsible for the mammalian neurotoxicity associated with the ingestion of nitrogen trichloride bleached flour. Methionine sulfoximine was ...