Use of N-Boc-tert-butyldimethylsilyoxypyrrole in highly diastereoselective aldol reaction

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1755-1758

  Pichon, Marianne ^a   Jullian, Jean Christophe ^a   Figadère, Bruno ^a   Cavé, André ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032568231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00058-6     Document Type: Article

References (16)

1. (1) Szlosek, M.; Franck, X.; Figadère, B. ; Cavé, A. J. Org. Chem. submitted.
2. (2) For isolation of muricatacin, see : Rieser, M.J.; Koslowski, J.F.; Wood, K.V.; McLauglin, J.L., Tetrahedron Lett., 1991, 32, 1137-1141; for total synthesis of muricatacin see references cited in : Figadère, B., Acc. Chem. Res., 1995, 28, 359-365, and : Somfai, P., J. Chem. Soc. Trans I, 1995, 817; Quayle, P.; Rahman, S.; Herbert, J., Tetrahedron Lett. 1995, 36, 8087. For the most recent review on annonaceous acetogenins, see : Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D., In Progress in the Chemistry Of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, New York, 1997, Vol. 70, pp 81-288
3. (2) For isolation of muricatacin, see : Rieser, M.J.; Koslowski, J.F.; Wood, K.V.; McLauglin, J.L., Tetrahedron Lett., 1991, 32, 1137-1141; for total synthesis of muricatacin see references cited in : Figadère, B., Acc. Chem. Res., 1995, 28, 359-365, and : Somfai, P., J. Chem. Soc. Trans I, 1995, 817; Quayle, P.; Rahman, S.; Herbert, J., Tetrahedron Lett. 1995, 36, 8087. For the most recent review on annonaceous acetogenins, see : Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D., In Progress in the Chemistry Of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, New York, 1997, Vol. 70, pp 81-288
4. (2) For isolation of muricatacin, see : Rieser, M.J.; Koslowski, J.F.; Wood, K.V.; McLauglin, J.L., Tetrahedron Lett., 1991, 32, 1137-1141; for total synthesis of muricatacin see references cited in : Figadère, B., Acc. Chem. Res., 1995, 28, 359-365, and : Somfai, P., J. Chem. Soc. Trans I, 1995, 817; Quayle, P.; Rahman, S.; Herbert, J., Tetrahedron Lett. 1995, 36, 8087. For the most recent review on annonaceous acetogenins, see : Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D., In Progress in the Chemistry Of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, New York, 1997, Vol. 70, pp 81-288
5. (2) For isolation of muricatacin, see : Rieser, M.J.; Koslowski, J.F.; Wood, K.V.; McLauglin, J.L., Tetrahedron Lett., 1991, 32, 1137-1141; for total synthesis of muricatacin see references cited in : Figadère, B., Acc. Chem. Res., 1995, 28, 359-365, and : Somfai, P., J. Chem. Soc. Trans I, 1995, 817; Quayle, P.; Rahman, S.; Herbert, J., Tetrahedron Lett. 1995, 36, 8087. For the most recent review on annonaceous acetogenins, see : Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D., In Progress in the Chemistry Of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, New York, 1997, Vol. 70, pp 81-288
6. (2) For isolation of muricatacin, see : Rieser, M.J.; Koslowski, J.F.; Wood, K.V.; McLauglin, J.L., Tetrahedron Lett., 1991, 32, 1137-1141; for total synthesis of muricatacin see references cited in : Figadère, B., Acc. Chem. Res., 1995, 28, 359-365, and : Somfai, P., J. Chem. Soc. Trans I, 1995, 817; Quayle, P.; Rahman, S.; Herbert, J., Tetrahedron Lett. 1995, 36, 8087. For the most recent review on annonaceous acetogenins, see : Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D., In Progress in the Chemistry Of Natural Products; Herz, W., Eds.; Springer-Verlag: Wien, New York, 1997, Vol. 70, pp 81-288
7. (3) Baussanne, I.; Schwardt, O.; Royer, J.; Pichon, M.; Figadère, B.; Cavé, A.; Tetrahedron Lett. 1997, 38, 2259-2262
8. (4) Cavé, A.; Chaboche, C.; Figadère, B.; Harmange, J.-C.; Laurens, A.; Peyrat, J.F.; Pichon, M.; Szlosek, M.; Cotte-Lafitte, J.; Quéro, A.M. Eur. J. Med. Chem. 1997, 32, 617-623.
9. (5) Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G., J. Org. Chem., 1997, 62, 4513-4517.
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11. 3, see : Resek, I.E.; Meyers, A.I. Tetrahedron Lett. 1995, 36, 7051-7054.
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13. 3)). (graph presented)
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16. (12) For some studies on these complexes in the Mikami Ene reaction, see : Corey, E.J.; Barnes-Seeman, D.; Lee, T.W.; Goodman, S.N. Tetrahedron Lett. 1997, 37, 6513-6516.