New synthesis of (±)-sitophilate using carboxylic acid dianion methodology - A stereoselectivity study

Synthesis

Volumn , Issue 19, 2005, Pages 3451-3455

  Gil, Salvador ^a   Parra, Margarita ^a   Rodriguez, Pablo ^a   Sotoca, Enrique ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Addition reaction; Aldehyde; Amino alcohols; Carboxylic acids; Diastereoselectivit

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; AMINES; ESTERIFICATION; ISOMERS; NEGATIVE IONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AMINO ALCOHOLS; CHIRAL AMIDES; DIASTEREOSELECTIVIT; PROPANOIC ACID;

CARBOXYLIC ACIDS;

AMIDE; ANION; CARBOXYLIC ACID; LITHIUM DERIVATIVE; LITHIUM ENEDIOLATE; PHEROMONE; PROPIONALDEHYDE; PROPIONIC ACID DERIVATIVE; SITOPHILATE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; DIASTEREOISOMER; ESTERIFICATION; ISOMER; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

EID: 29044433695     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918466     Document Type: Article

References (36)

1. Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton, 1994, 87-184.
2. Clayden, J. Organolithiums: Selectivity for Synthesis', Pergamon Press: Oxford, 2002, 73-86.
3. Streitwieser, A.; Husemann, M.; Kim, Y.-J. J. Org. Chem. 2003, 68, 7937.
4. Gil, S.; Parra, M. Curr. Org. Chem. 2002, 6, 283.
5. Gil, S.; Parra, M. Recent Res. Dev. Org. Chem. 2002, 6, 449.
6. Brun, E. M.; Casades, I.; Gil, S.; Mestres, R.; Parra, M. Tetrahedron Lett. 1998, 39, 5443.
7. Parra, M.; Sotoca, E.; Gil, S. Eur. J. Org. Chem. 2003,1386.
8. Sotoca, E.; Bouillon, J. P.; Gil, S.; Parra, M.; Portella, C. Tetrahedron Lett. 2004, 45, 8315.
9. Mekelburger, H. B.; Wilcos, C. S. Formation of Enolates, In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 99-131.
10. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopedhyay, T.; Simon, M.; Seebach, D. Synthesis 1993, 1271.
11. Eames, J. Eur. J. Org. Chem. 2002, 393.
12. Streitwieser, A.; Pratt, L. M. J. Org. Chem. 2003, 68, 7937.
13. Streitwieser, A.; Facchetti, A. J. Org. Chem. 2004, 69, 8345.
14. Scott, R.; Gremader, J.; Dimer, P.; Hilmersson, G. Tetrahedron: Asymmetry 2004, 15, 267.
15. Streitwieser, A.; Weng, Z.-R. J. Am. Chem. Soc. 1999,121, 6213.
16. Balomrju, Y.; Sharp, C. D.; Gammill, W.; Manuel, N.; Pratt, L. M. Tetrahedron 1998, 54, 7357.
17. Brun, E. M.; Gil, S.; Parra, M. Tetrahedron: Asymmetry 2001,12, 915.
18. Brun, E. M.; Gil, S.; Mestres, R.; Parra, M. Synlett 2001, 156.
19. Eames, J.; Suggate, M. J. Angew. Chem. Int. Ed. 2005, 44, 186.
20. Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998,120, 4081.
21. Phillips, J. K.; Miller, S. P. F.; Andersen, J. F.; Fales, H. M.; Burkholder, W. E. Tetrahedron Lett. 1987, 28, 6145.
22. Mori, K.; Ishikura, M. Liebigs Ann. Chem. 1989, 1263.
23. Chang, J. M. Tetrahedron 1989, 45, 623.
24. Sugai, T.; Sakuma, D.; Kobayashi, N.; Ohta, H. Tetrahedron 1991, 47, 7237.
25. Cheskis, B. A.; Shpiro, N. A.; Noiseenkov, M. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl, Transl.) 1991, 40, 2205.
26. Razkin, J.; Gonzalez, A.; Gil, P. Tetrahedron: Asymmetry 1996, 7, 3479.
27. Gil, P.; Razkin, J.; Gonzalez, A. Synthesis 1998, 386.
28. Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P. Tetrahedron 2001, 57, 6901.
29. Mitsunobu, O. Synthesis 1981, 1.
30. Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 656.
31. (a) Mi, A. Q.; Wang, Z.-Y.; Jiang, Y. Z. Tetrahedron: Asymmetry 1993, 4, 1957.
32. (b) Matsuo, J.-i.; Koga, K. Chem. Pharm. Bull. 1997, 45, 2122.
33. Mulzer, J.; Zippel, M.; Brüntrop, G.; Seguer, J.; Finke, J. Liebigs Ann. Chem. 1980, 1108.
34. Murakata, M.; Yasukata, T.; Aoki, T.; Nakajima, M.; Koga, K. Tetrahedron 1998, 54, 2449.
35. Chou, T. Q. J. Biol. Chem. 1926, 70, 109.
36. Nishida, A.; Shirato, F.; Nakagawa, M. Tetrahedron: Asymmetry 2000,11, 3789.