Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine.

reaction: see text] The asymmetric synthesis and chemical modification of p-bromophenyl methyl sulfoximine (2) is described. Starting from p-bromophenyl menthyl sulfinate (5), enantiopure 2 can be obtained in a short reaction sequence involving a well-established substitution reaction followed by stereospecific imination with O-mesitylenesulfonylhydroxylamine (MSH). Palladium-catalyzed Buchwald/Hartwig, Suzuki, and Stille coupling reactions allow a broad variation of the sulfoximine aryl group, which is otherwise difficult to achieve. The incorporation of a p-morpholino-substituted derivative into a pseudotripeptide demonstrates the applicability of the novel sulfoximine derivatives.

Citation

Gae Young Cho, Hiroaki Okamura, Carsten Bolm. Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine. The Journal of organic chemistry. 2005 Mar 18;70(6):2346-9

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PMID: 15760228

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