An expeditious enantioselective synthesis of methyl trans-chrysanthemate

Synthesis

Volumn , Issue 14, 2002, Pages 2019-2022

  Krief, Alain ^a   Dumont, Willy ^a   Baillieul, Diane ^b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b Fonds pour la formation à la Recherche dans l'Industrie et dans l'Agriculture FRIA   (Belgium)

Author keywords

Asymmetric induction; Cyclopropanation; Sharpless epoxidation; Sulfur ylides

Indexed keywords

ORGANIC COMPOUNDS;

EPOXIDATION REACTION;

SYNTHESIS (CHEMICAL);

3 (3,3 DIMETHYLOXIRAN 2 YL)PROP 2 ENOATE; ACRYLIC ACID DERIVATIVE; ISOPROPYLIDENEDIPHENYLSULFURANE; METHYLCHRYSANTHEMATE; PHOSPHORANE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL MODIFICATION; ENANTIOSELECTIVITY; EPOXIDATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 0036398492     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34388     Document Type: Article

References (26)

1. (a) Krief, A.; Bayet, P.; Hevesi, L.; Devos, M.-J. Tetrahedron Lett. 1976, 3911.
2. (b) Krief, A.; Hevesi, L.; Sevrin, M. Tetrahedron Lett. 1976, 3918.
3. (a) Krief, A.; Devos, M.-J. Tetrahedron Lett. 1979, 1511.
4. (b) Krief, A.; Devos, M.-J. Tetrahedron Lett. 1979, 1518.
5. Krief, A.; Lecomte, P.; Demoute, J. P.; Dumont, W. Synthesis 1990, 275.
6. (a) Mulzer, J.; Kappert, M. Angew. Chem., Int. Ed. Engl. 1983, 22, 63.
7. (b) Krief, A.; Dumont, W.; Pasau, P. Tetrahedron Lett. 1988, 29, 1079.
8. (c) Krief, A.; Dumont, W. Tetrahedron Lett. 1988, 29, 1083.
9. (d) Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039.
10. (e) Krief, A.; Surleraux, D.; Dumont, W.; Pasau, P.; Lecomte, P. In Strain and Its Application in Organic Chemistry; de Meijere, A.; Blechert, S., Eds.; Kluwer Academic Publishers: Dordrecht, 1989, 333.
11. (f) Bernardi, A.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1989, 30, 3733.
12. (g) Krief, A.; Surleraux, D.; Dumont, W.; Pasau, P.; Lecomte, P. Pure Appl. Chem. 1990, 62, 1311.
13. (h) Leonard, J. Contemp. Org. Synth. 1994, 1, 387.
14. (i) Leonard, J.; Mohialdin, S.; Reed, D.; Ryan, G.; Swain, P. A. Tetrahedron 1995, 51, 12843.
15. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 2002, in press.
16. (a) Krief, A.; Denis, J.-N.; Magnane, R.; van Eenoo, M. Nouv. J. Chim. 1979, 3, 705.
17. (b) Suzuki, H.; Fuchita, T.; Iwasa, A.; Mishina, T. Synthesis 1978, 905.
18. (a) Molander, G. A. Org. React. 1995, 46, 211.
19. (b) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
20. Work is in progress to understand the scope and limitation of this reaction.
21. (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
22. (b) Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Org. Chem. 1987, 52, 667.
23. (c) Uchiro, H.; Nagasawa, K.; Aiba, Y.; Kotake, T.; Hasegawa, D.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 4531.
24. (a) Parikh, J. R.; von Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505.
25. (b) Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
26. House, H. O.; Jones, V. K.; Frank, G. A. J. Org. Chem. 1964, 29, 3327.