Preparation of 3,3-bis(tributylstannyl)propenes, potential new 1,3-allyl dianions

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6657-6660

  Madec, David ^a   Ferezou, Jean Pierre ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; ORGANOTIN COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030880841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01558-X     Document Type: Article

References (38)

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23. 6 was obtained by IBX oxidation (91% yield) of the corresponding 3-hydroxy-1-alkenyl carbamate: Madec, D.; Férézou, J.-P. Synlett 1996, 867-870. For IBX oxidation, see: Frigerio, M.; Santagostino, M. Tetrahedron Lett., 1994, 35, 8019-8022. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
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26. Pure (E)-3-(4-methoxyphenylthio)prop-2-enal 7 has been prepared in 94% yield from methyl propiolate : Grimaud, L.; Férézou, J.-P.; Prunet, J.; Lallemand, J.-Y. Tetrahedron 1997, 9253-9268.
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29. Cabezas, J.A.; Oehlschlager, A.C. Synthesis 1994, 432-442. Cabezas, J.A.; Oehlschlager, A.C. J. Am. Chem. Soc. 1997, 119, 3878-3886.
30. Wender, P.A.; Sieburth, S. McN.; Petraitis, J.J.; Singh, S.K. Tetrahedron 1981, 37, 3967-3975. Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153. For the synthesis of 3,3-diethoxyprop-1-yne, see : Le Cocq, A.; Gorgues, A. in Organic Synthesis; Wiley: New York, 1988, Coll. Vol. VI, p 954. For mixed higher order cuprate addition to 13 : Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333-6336; Marek, I.; Alexakis, a.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337-6340. For a recent application of aldehyde 12, see Lipshutz, B.H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
31. Wender, P.A.; Sieburth, S. McN.; Petraitis, J.J.; Singh, S.K. Tetrahedron 1981, 37, 3967-3975. Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153. For the synthesis of 3,3-diethoxyprop-1-yne, see : Le Cocq, A.; Gorgues, A. in Organic Synthesis; Wiley: New York, 1988, Coll. Vol. VI, p 954. For mixed higher order cuprate addition to 13 : Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333-6336; Marek, I.; Alexakis, a.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337-6340. For a recent application of aldehyde 12, see Lipshutz, B.H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
32. Wender, P.A.; Sieburth, S. McN.; Petraitis, J.J.; Singh, S.K. Tetrahedron 1981, 37, 3967-3975. Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153. For the synthesis of 3,3-diethoxyprop-1-yne, see : Le Cocq, A.; Gorgues, A. in Organic Synthesis; Wiley: New York, 1988, Coll. Vol. VI, p 954. For mixed higher order cuprate addition to 13 : Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333-6336; Marek, I.; Alexakis, a.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337-6340. For a recent application of aldehyde 12, see Lipshutz, B.H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
33. Wender, P.A.; Sieburth, S. McN.; Petraitis, J.J.; Singh, S.K. Tetrahedron 1981, 37, 3967-3975. Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153. For the synthesis of 3,3-diethoxyprop-1-yne, see : Le Cocq, A.; Gorgues, A. in Organic Synthesis; Wiley: New York, 1988, Coll. Vol. VI, p 954. For mixed higher order cuprate addition to 13 : Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333-6336; Marek, I.; Alexakis, a.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337-6340. For a recent application of aldehyde 12, see Lipshutz, B.H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
34. Wender, P.A.; Sieburth, S. McN.; Petraitis, J.J.; Singh, S.K. Tetrahedron 1981, 37, 3967-3975. Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153. For the synthesis of 3,3-diethoxyprop-1-yne, see : Le Cocq, A.; Gorgues, A. in Organic Synthesis; Wiley: New York, 1988, Coll. Vol. VI, p 954. For mixed higher order cuprate addition to 13 : Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333-6336; Marek, I.; Alexakis, a.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337-6340. For a recent application of aldehyde 12, see Lipshutz, B.H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
35. Wender, P.A.; Sieburth, S. McN.; Petraitis, J.J.; Singh, S.K. Tetrahedron 1981, 37, 3967-3975. Ostwald, R.; Chavant, P.-Y.; Stadtmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153. For the synthesis of 3,3-diethoxyprop-1-yne, see : Le Cocq, A.; Gorgues, A. in Organic Synthesis; Wiley: New York, 1988, Coll. Vol. VI, p 954. For mixed higher order cuprate addition to 13 : Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333-6336; Marek, I.; Alexakis, a.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337-6340. For a recent application of aldehyde 12, see Lipshutz, B.H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555-4556.
36. For recent synthetic applications of 15, see : Gómez-Sánchez, A.; Hermosín, I.; Lassaletta, J.-M.; Maya, I. Tetrahedron 1993, 49, 1237-1250 and references cited therein.
37. David S., Lubineau A., Vatèle J.-M. New. J. Chem. 4:1980;547-558.
38. Madec, D.; Férézou, J.-P. Tetrahedron Lett. 1997, next paper.