Asymmetric synthesis of cyclopropane-1,1-dicarboxylates from a -γ- Alkoxy-alkylidenemalonate

Synlett

Volumn , Issue 12, 1999, Pages 1936-1938

  Krief, Alain ^a   Provins, Laurent ^a   Froidbise, Alexandre ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

Asymmetric synthesis; Cyclopropane derivative; Michael adduct

Indexed keywords

CYCLOPROPANE DERIVATIVE; DICARBOXYLIC ACID; MALONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032714943     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3173     Document Type: Article

References (19)

1. (a) Yechezkel, T.; Ghera, E.; Ramesh, N. G.; Hassner, A. Tetrahedron: Asymmetry 1996, 7, 2423.
2. (b) Ferreira, A. R. G.; Dias, A. G.; Pinto, A. C.; Costa, P. R. R.; Miguez, E.; da Silva, A. J. R. Tetrahedron Lett. 1998, 39, 5305.
3. (c) Costa, J. S.; Dias, A. G.; Anholeto, A. L.; Monteiro, M. D.; Patrocinio, V. L.; Costa, P. R. R. J. Org. Chem. 1997, 62, 4002.
4. Krief, A.; Hevesi, L.; Chaboteaux, G.; Mathy, P.; Sevrin, M.; DeVos, M.-J. J. Chem. Soc., Chem. Commun. 1985, 1693.
5. (b) Chaboteaux, G.; Krief, A. Bull. Soc. Chim. Belg. 1985, 94, 495.
6. (c) Krief, A.; DeVos, M.-J. Tetrahedron Lett. 1985, 26, 6115.
7. (d) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226.
8. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437 and references cited.
9. 2-metallo-2-nitropropanes are better described as nitronates anions. Description as 2-metallo-2-nitropropanes in the text is only used for consistency and does not reflect the reality.
10. (a) Krief, A. in "Organic Synthesis. A Chemistry for the 21st Century Monograph", International Union of Pure and Applied Chemistry, Trost, B. M., Ed; Blackwell Scientific Publications 1994, 337.
11. (b) Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039.
12. (c) Mulzer, J.; Kappert, M. Angew. Chem. Int. Ed. Engl. 1983, 22, 63.
13. 7
14. 3.
15. 7
16. (a) Baudoux, G.; Norberg, B.; Provins, L.; Froidbise, A.; Krief, A.; Evrard G. Acta Cryst. 1998, C54, 834.
17. SSi does not cyclize when heated at 80 °C in THF-HMPA.
18. Si Rt = 5.3 min.
19. NSi is formed in 70% yield when the reaction is performed in THF-HMPA.