Catalytic asymmetric vinylogous Mukaiyama (CAVM) reactions: Aldehyde activation versus enolate activation

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5507-5509

  Bluet, Guillaume ^a   Campagne, Jean Marc ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY;

EID: 0033165962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01070-9     Document Type: Article

References (15)

1. Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. In Stereoselective Synthesis; Thieme: Stuttgart, 1996; Vol. 3.
2. Heathcock, C. H. In Asymmetric Synthesis; Morrisson, J. D., Ed.; Academic Press: San Diego, CA, 1984.
3. Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365.
4. For a comprehensive review, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
5. For the use of cyclic vinylogous-enolate, see (and references cited therein): (a) Pichon, M.; Jullian, J.-C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1998, 39, 1755.
6. (b) Dudot, B.; Micouin, L.; Baussane, I.; Royer, J. Synthesis 1999, 688.
7. For the use of aceto-acetate dienolate derivatives in catalytic asymmetric aldol reactions using a chiral Lewis acid, see: Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
8. For the use of aceto-acetate dienolate derivatives in catalytic asymmetric aldol reactions using an enolate activation, see: (a) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
9. (b) Pagenkopf, B. L.; Kruger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3124.
10. For elegant alternatives, see: (a) Black, W. C.; Giroux, A.; Greidanus, G. Tetrahedron Lett. 1996, 37, 4471.
11. (b) Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1996, 37, 8895.
12. For some applications of the racemic vinylogous Mukaiyama reaction in the synthesis of natural products, see: (a) Paterson, I.; Smith, J. D. J. Org. Chem. 1992, 57, 3261.
13. (b) Patron, A. P.; Richter, P. K.; Tomaszewski, M. J.; Miller, R. A.; Nicolaou, K. C. J. Chem. Soc., Chem. Commun. 1994, 1147.
14. (c) Mouné, S.; Niel, G.; Busquet, M.; Eggleston, I.; Jouin, P. J. Org. Chem. 1997, 62, 3332.
15. Fleming, I.; Leslie, C. P. J. Chem. Soc., Perkin Trans. 1 1996, 1198.