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Stereoselective Reactions of Lithium and Zinc tert-Butyl Phenylmethyl Sulfoxide with Carbonyl Compounds and Imines1

Journal Article


Abstract


  • Racemic lithium tert-butyl phenylmethyl sulfoxide 1A when quenched with benzophenone gives CR*SR*-2-tert-butylsulfmyl)-1,1,2-triphenylethanol as determined by single-crystal X-ray analysis. The diastereoselection in the reaction of 1A with various aldehydes and imines as a function of aldehyde and imline structure and metal cation (Li+or Zn2+) is reported. Both substrates show a preference for anti diastereoselection. Transition-state structures are proposed to account for this diastereoselection. © 1989, American Chemical Society. All rights reserved.

Publication Date


  • 1989

Citation


  • Pyne, S. G., & Boche, G. (1989). Stereoselective Reactions of Lithium and Zinc tert-Butyl Phenylmethyl Sulfoxide with Carbonyl Compounds and Imines1. Journal of Organic Chemistry, 54(11), 2663-2667. doi:10.1021/jo00272a040

Scopus Eid


  • 2-s2.0-0001662661

Web Of Science Accession Number


Start Page


  • 2663

End Page


  • 2667

Volume


  • 54

Issue


  • 11

Abstract


  • Racemic lithium tert-butyl phenylmethyl sulfoxide 1A when quenched with benzophenone gives CR*SR*-2-tert-butylsulfmyl)-1,1,2-triphenylethanol as determined by single-crystal X-ray analysis. The diastereoselection in the reaction of 1A with various aldehydes and imines as a function of aldehyde and imline structure and metal cation (Li+or Zn2+) is reported. Both substrates show a preference for anti diastereoselection. Transition-state structures are proposed to account for this diastereoselection. © 1989, American Chemical Society. All rights reserved.

Publication Date


  • 1989

Citation


  • Pyne, S. G., & Boche, G. (1989). Stereoselective Reactions of Lithium and Zinc tert-Butyl Phenylmethyl Sulfoxide with Carbonyl Compounds and Imines1. Journal of Organic Chemistry, 54(11), 2663-2667. doi:10.1021/jo00272a040

Scopus Eid


  • 2-s2.0-0001662661

Web Of Science Accession Number


Start Page


  • 2663

End Page


  • 2667

Volume


  • 54

Issue


  • 11