Stereoselective Horner-Wittig synthesis of (Z)-1-chlorovinyl sulfoxides

Tetrahedron

Volumn 53, Issue 30, 1997, Pages 10527-10544

  Otten, Pieter A ^a   Davies, Honorine M ^a   Van Steenis, Jan Hein ^a   Gorter, Syb ^a   Van Der Gen, Arne ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOCHLORINE DERIVATIVE; SULFOXIDE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030842130     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00665-0     Document Type: Article

References (35)

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7. Horner-Wittig synthesis of (E)-vinyl sulfoxides: Van Es, J.J.G.S. 1,3-Cycloaddition Reactions of Diphenylphosphinoyl-activated Azomethine Ylides and 2-Azaallyl Anions, Thesis, Leiden University 1992; Horner-Wittig synthesis of (E)-α,β-unsaturated nitriles: Loupy, A.; Sogadji, K.; Seyden-Penne, J. Synthesis, 1977, 126-127; Etemad-Moghadam, G.; Seyden-Penne, J. Synth. Commun. 1984, 14, 565-573; Horner-Wittig synthesis of di-and tri-substituted α,β-unsaturated esters with excellent E-selectivity: Etemad-Moghadam, G.; Seyden-Penne, J. Tetrahedron 1985, 40, 5153-5166.
8. Horner-Wittig synthesis of (E)-vinyl sulfoxides: Van Es, J.J.G.S. 1,3-Cycloaddition Reactions of Diphenylphosphinoyl-activated Azomethine Ylides and 2-Azaallyl Anions, Thesis, Leiden University 1992; Horner-Wittig synthesis of (E)-α,β-unsaturated nitriles: Loupy, A.; Sogadji, K.; Seyden-Penne, J. Synthesis, 1977, 126-127; Etemad-Moghadam, G.; Seyden-Penne, J. Synth. Commun. 1984, 14, 565-573; Horner-Wittig synthesis of di-and tri-substituted α,β-unsaturated esters with excellent E-selectivity: Etemad-Moghadam, G.; Seyden-Penne, J. Tetrahedron 1985, 40, 5153-5166.
9. Horner-Wittig synthesis of (E)-vinyl sulfoxides: Van Es, J.J.G.S. 1,3-Cycloaddition Reactions of Diphenylphosphinoyl-activated Azomethine Ylides and 2-Azaallyl Anions, Thesis, Leiden University 1992; Horner-Wittig synthesis of (E)-α,β-unsaturated nitriles: Loupy, A.; Sogadji, K.; Seyden-Penne, J. Synthesis, 1977, 126-127; Etemad-Moghadam, G.; Seyden-Penne, J. Synth. Commun. 1984, 14, 565-573; Horner-Wittig synthesis of di-and tri-substituted α,β-unsaturated esters with excellent E-selectivity: Etemad-Moghadam, G.; Seyden-Penne, J. Tetrahedron 1985, 40, 5153-5166.
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14. Di-p-(trifluoromethyl)phenyldisulfide was prepared according to a literature procedure for diphenyldiselenide, using p-(trifluoromethyl)bromobenzene and elemental sulfur: Reich, H.J.; Cohen, M.L.; Clark, P.S. Organic Synthesis 1979, 59, 141-147; Reich, H.J. Renga, M.J.; Reich, I. J. Am. Chem. Soc. 1975, 97, 5434-5447.
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18. 5.
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23. d) For treatment of 1-chlorovinyl sulfones with KOt-Bu to yield acetylenic sulfones, see: Lee, J.W.; Kim, T.H.; Oh, D.Y. Synth. Commun. 1989, 19, 2633-2637; Lee, J.W.; Oh, D.Y. Synth. Commun. 1990, 20, 273-277.
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26. Major contributions towards the elucidation of the mechanism of the Horner-Wittig (and HWE) reaction and the factors that determine the stereoselectivity are due to Professor Jacqueline Seyden-Penne and her co-workers: a) Seyden-Penne, J.; Lefebvre, G. Compt. Rend. 1969, 269, C48-50;
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