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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 18
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Original Articles

Optically Active Alkylvinylpyridines: Synthesis of (+)-(S)-6-(1-Methylpropyl)-2-Vinylpyridine

Pages 2645-2651 | Received 08 May 1992, Published online: 23 Sep 2006

References

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  • Hodge , P. and Sherrington , D. C. , eds. 1980 . Polymer-Supported Reactions in Organic Synthesis , New. York : Wiley . Akelah, A., Sherrington, D. C. Chem. Rev., 1981, 81, 557
  • Wright , M. E. and Pulley , S. R. 1987 . J. Org. Chem. , 52 : 5036 and references therein
  • Charmot , D. , Audebert , R. and Quivoron , C. 1986 . J. Polym. Sci., Polym. Lett. , 24 : 59
  • Botteghi , C. , Caccia , G. and Gladiali , S. 1979 . Synth. Commun. , 9 : 69
  • Seeman , J. I. , Chavdarian , C. G. , Kornfeld , R. A. and Naworal , J. D . 1985 . Tetrahedron , 41 : 595
  • Chelucci , G. Gazz. Chim. Ital. , For a review, see, in press
  • (+)-(S)-2-Methylbutanenitrile has been prepared through oxidation of the naturally occurring (-)-(S)-2-methyl-1-butanol, followed by dehydration with chlorosulfonyl isocyanate13 of the obtained (+)-(S)-2-methylbutanoic acid. For the preparation of (+)-(S)-2-(1-methylpropyl)pyridine (2) a sample of (+)-(S)-2-methylbutanenitrile having [α]25D +30.4° (neat; 78% optical purity) has been used
  • Tatone , D. , Dich , T. C. , Nacco , R. and Botteghi , C. 1975 . J. Org. Chem. , 40 : 2987
  • Azzena , U. , Delogu , G. , Gladiali , S. , Marchetti , M. , Soccolini , F. and Botteghi , C. 1986 . Gazz. Chim. Ital. , 116 : 307 For the preparation of a number of optically active 2-alkylpyridines by this method, see
  • Fife , W. K. 1983 . J. Org. Chem. , 48 : 1375
  • Lardicci , L. , Botteghi , C. and Salvadori , P. 1968 . Gazz. Chim. Ital. , 98 : 760 Botteghi, C.; Guetti, E.; Ceccarelli, G.; Lardicci, L. ibid., 1972, 102, 945
  • Botteghi , C. , Chelucci , G. and Marchetti , M. 1982 . Synth. Commun. , 12 : 25
  • Botteghi , C. , Caccia , G. , Chelucci , G. and Soccolini , F. 1984 . J. Org. Chem. , 49 : 4290

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