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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 4
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Original Articles

Synthesis of New Chiral Vinyl Halides from L-Serinal

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Pages 613-622 | Received 24 Jul 1997, Published online: 02 Sep 2006

References

  • Furber M. “Acetylenes”, and Urch, C. J. “Vinyl and Aryl Halides” in “Comprehensive Organic Functional Group Transformations”, Pergamon, Katritzky, A. R.; Meth-Cohn, O. and Rees, C. W. Editors-in-Chief, vol. 1 and 2 respectively.
  • Ramiandrasoa , P. , Bréhon , B. , Thivet , A. , Alami , M. and Cahiez , G. 1997 . Tetrahedron Lett. , 38 : 2447
  • Alami , M. , Crousse , B. and Linstrumelle , G. 1995 . Tetrahedron Lett. , 36 : 3687
  • Uenishi , J. , Kawahama , R. , Shiga , Y. and Yonemitsu , O. 1996 . Tetrahedron Lett. , 37 : 6759
  • Reginato , G. , Mordini , A. , Messina , F. , Degl'Innocenti , A. and Poli , G. 1996 . Tetrahedron , 52 : 10985
  • Meffre , P. , Gauzy , L. , Perdigues , C. , Desanges-Levecque , F. , Branquet , E. , Durand , P. and Le Goffic , F. 1995 . Tetrahedron Lett. , 36 : 877
  • Meffre , P. , Gauzy , L. , Branquet , E. , Durand , P. and Le Goffic , F. 1996 . Tetrahedron , 52 : 11215
  • Corey , E. J. and Fuchs , P. L. 1972 . Tetrahedron Lett. , : 3769
  • Reginato , G. , Mordini , A. , Degl'Innocenti , A. and Caracciolo , M. 1995 . Tetrahedron Lett. , 36 : 8275 – 8278 . ibid 1996 37 1325
  • Chung , J. Y. L. and Wasicak , J. T. 1990 . Tetrahedron Lett. , 31 : 3957
  • Grandjean , D. , Pale , P. and Chuche , J. 1994 . Tetrahedron Lett. , 35 : 3529
  • Jiang , B. and Ma , P. 1995 . Synth. Commun. , 25 ( 22 ) : 3641
  • Miyano , S. , Izumi , Y. and Hashimoto , H. 1978 . J. Chem. Soc. Chem. Commun. , : 446
  • Mella , M. , Panza , L. , Ronchetti , F. and Toma , L. 1988 . Tetrahedron , 44 : 1673
  • Matsumoto , M. and Kuroda , K. 1980 . Tetrahedron Lett. , 21 : 4021
  • McCarthy , J. R. , Huber , E. W. , Le , T.-B. , Laskovics , F. M. and Matthews , D. P. 1996 . Tetrahedron , 52 : 45 The fluorine containing analogues have recently been described:
  • Grandjean , D. and Pale , P. 1993 . Tetrahedron Lett. , 34 : 1155
  • Harada , T. , Katsuhira , T. and Oku , A. 1992 . J. Org. Chem. , 57 : 5805
  • For a stereoselective synthesis of (Z)-vinyl bromides see ref. 2c.
  • In our hands, alkyne 2 is obtained with a maximum 50% yield when 2eq. nBuLi is aded slowly on a THF solution of dibromovinyl derivative 3, at −78°C. 2 is often contaminated with vinyl bromide 4 and with enamine 9.5a Formation of 9 is probably due to abstraction of the proton with enhanced acidity α to NBoc (see Beak, P.; Lee, W.-K.Tetrahedron Lett. 1989 30 1197) with concomitant acetone elimination. We also observed this reaction with other oxazolidines derived from L-serinal 1 with a double or a triple bond in the 4-position.3b Unstable enamine 9 is obtained in 65% yield if alkyne 2 is treated with excess nBuLi in THF. 9: 1H-NMR (200MHz, CDCl3, δ in ppm): 1.49 (s, 9H); 2.88 (s, 1H); 5.05 (s, 1H); 5.82 (s, 1H); 6.0 (brs, 1H). MS (DCI, NH3) 185 (M+NH4)+, 168 (M+H)+, 129 (M-tBu+NH4)+.
  • Köbrich , G. 1965 . Angew. Chem. Int. Ed. Engl. , 4 : 49
  • Formation of enamine 9 (see note 11 above) is observed (crude yield ∼40%).
  • Beaulieu , P. L. , Duceppe , J.-S. and Johnson , C. 1991 . J. Org. Chem. , 56 : 4196
  • Mosher , H. S. and Dale , J. A. 1973 . J. Amer. Chem. Soc. , 95 : 512
  • Meffre , P. , Durand , P. , Branquet , E. and Le Goffic , F. 1994 . Synth. Comm. , 24 ( 15 ) : 2147
  • Branquet , E. , Durand , P. , Vo-Quang , L. and Le Goffic , F. 1993 . Synth. Comm. , 23 ( 2 ) : 153
  • Garner , P. and Park , J. M. 1992 . Org. Synth. , 70 : 18
  • Suffert , J. 1989 . J. Org. Chem. , 54 : 509
  • Martin , G. J. and Naulet , N. 1970 . Bull. Soc. Chim. Fr. , : 4001
  • Miller , R. B. and McGarvey , G. 1978 . J. Org. Chem. , 43 : 4424

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