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Chiral sulfur compounds. Part 25. Diastereoselective 1,2-additions of lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to ketones

Journal Article


Abstract


  • Lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 2f reacts with prochiral ketones to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts with a diastereoselection ranging from 79:21 to 98:2 depending upon the steric demand of the ketone. Racemic chiral cyclic ketones react with 2f to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts which could be separated by a combination of column chromatography and recrystallization. Thermolysis of the diastereoisomerically pure adducts gave 2-alkylcyclohexanones in high enantiomeric purity. The relative stereochemistries of four of the β-hydroxy sulfoximine adducts have been unequivocally determined from single-crystal X-ray structural analysis. The stereochemical outcome of these 1,2-additions can best be rationalized by invoking competing boat transition states.

Publication Date


  • 1994

Citation


  • Pyne, S. G., Dong, Z., Skelton, B. W., & White, A. H. (1994). Chiral sulfur compounds. Part 25. Diastereoselective 1,2-additions of lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to ketones. Journal of the Chemical Society, Perkin Transactions 1, (18), 2607-2613. doi:10.1039/p19940002607

Scopus Eid


  • 2-s2.0-37049080319

Web Of Science Accession Number


Start Page


  • 2607

End Page


  • 2613

Issue


  • 18

Abstract


  • Lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 2f reacts with prochiral ketones to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts with a diastereoselection ranging from 79:21 to 98:2 depending upon the steric demand of the ketone. Racemic chiral cyclic ketones react with 2f to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts which could be separated by a combination of column chromatography and recrystallization. Thermolysis of the diastereoisomerically pure adducts gave 2-alkylcyclohexanones in high enantiomeric purity. The relative stereochemistries of four of the β-hydroxy sulfoximine adducts have been unequivocally determined from single-crystal X-ray structural analysis. The stereochemical outcome of these 1,2-additions can best be rationalized by invoking competing boat transition states.

Publication Date


  • 1994

Citation


  • Pyne, S. G., Dong, Z., Skelton, B. W., & White, A. H. (1994). Chiral sulfur compounds. Part 25. Diastereoselective 1,2-additions of lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to ketones. Journal of the Chemical Society, Perkin Transactions 1, (18), 2607-2613. doi:10.1039/p19940002607

Scopus Eid


  • 2-s2.0-37049080319

Web Of Science Accession Number


Start Page


  • 2607

End Page


  • 2613

Issue


  • 18