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Chiral Sulfur compounds. xv. diastereoselective additions of lithiated s-benzyl-n-t-butyldiphenylsilyl-s-methyl-sulfoximine to imines and aldehydes

Journal Article


Abstract


  • The lithium salt of racemic S-benzyl-N-t- butyldiphenylsilyl-S-methylsulfoximine (2) undergoes 1, 2-addition to imines that have been activated by precomplexation with boron trifluoride diethyl etherate (BF3.Et2O), and aldehydes, with high diastereoselectivity. The relative lS*, 2S.*, S*s stereochemistry of the major diastereomeric adducts of (2) and EtCH = NPh and PriCH = NPh, and the relative lS*, 2S*, S*s stereochemistry of the major diastereomeric adduct of (2) and propanal were unequivocally determined by single-crystal X-ray structure analysis. An open transition state has been proposed to account for the stereochemical outcome of these reactions. © 1992 ASEG.

Publication Date


  • 1992

Citation


  • Pyne, S. G., & Dikic, B. (1992). Chiral Sulfur compounds. xv. diastereoselective additions of lithiated s-benzyl-n-t-butyldiphenylsilyl-s-methyl-sulfoximine to imines and aldehydes. Australian Journal of Chemistry, 45(5), 807-822. doi:10.1071/CH9920807

Scopus Eid


  • 2-s2.0-84970564793

Web Of Science Accession Number


Start Page


  • 807

End Page


  • 822

Volume


  • 45

Issue


  • 5

Abstract


  • The lithium salt of racemic S-benzyl-N-t- butyldiphenylsilyl-S-methylsulfoximine (2) undergoes 1, 2-addition to imines that have been activated by precomplexation with boron trifluoride diethyl etherate (BF3.Et2O), and aldehydes, with high diastereoselectivity. The relative lS*, 2S.*, S*s stereochemistry of the major diastereomeric adducts of (2) and EtCH = NPh and PriCH = NPh, and the relative lS*, 2S*, S*s stereochemistry of the major diastereomeric adduct of (2) and propanal were unequivocally determined by single-crystal X-ray structure analysis. An open transition state has been proposed to account for the stereochemical outcome of these reactions. © 1992 ASEG.

Publication Date


  • 1992

Citation


  • Pyne, S. G., & Dikic, B. (1992). Chiral Sulfur compounds. xv. diastereoselective additions of lithiated s-benzyl-n-t-butyldiphenylsilyl-s-methyl-sulfoximine to imines and aldehydes. Australian Journal of Chemistry, 45(5), 807-822. doi:10.1071/CH9920807

Scopus Eid


  • 2-s2.0-84970564793

Web Of Science Accession Number


Start Page


  • 807

End Page


  • 822

Volume


  • 45

Issue


  • 5