Highly diastereoselective synthesis of β-hydroxy amides from β-keto amides

Synthesis

Volumn , Issue 18, 2004, Pages 3092-3096

  Bartoli, Giuseppe ^a   Bosco, Marcella ^a   Marcantoni, Enrico ^b   Massaccesi, Massimo ^a   Rinaldi, Samuele ^c   Sambri, Letizia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF CAMERINO   (Italy)

^c UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Boranes; Diastereoselectivity; Hydroxy amides; Organocerium reagents; TiCl4

Indexed keywords

ALCOHOLS; MOLECULAR STRUCTURE;

AMIDES; DIASTEREOSELECTIVE SYNTHESIS; NATURAL PRODUCTS; TERTIARY ALCOHOLS;

KETONES;

ALCOHOL DERIVATIVE; AMIDE; BETA HYDROXY AMIDE; BETA KETO AMIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEOMETRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 11144321989     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829192     Document Type: Article

References (34)

1. Jacobson, I. C.; Reddy, P. G.; Wasserman, Z. R.; Hardman, K. D.; Covington, M. B.; Arner, E. C.; Copeland, R. A.; Decicco, C. P.; Magolda, R. Bioorg. Med. Chem. Lett. 1998, 8, 837.
2. Kakei, H.; Nemoto, T.; Ohshima, T.; Shibasaki, M. Angew. Chem. Int. Ed. 2004, 43, 317.
3. (a) Heathcock, C. H. In Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: New York, 1984, 111.
4. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1984, 13, 1.
5. (c) Evans, D. A.; McGee, L. R. Tetrahedron Lett. 1980, 21, 3975.
6. (d) Goasdoue, C.; Goasdoue, N.; Gaudemar, M. J. Organomet. Chem. 1981, 208, 279.
7. (e) Canceill, J.; Jacques, J. Bull. Soc. Chim. Fr. 1970, 2180.
8. (f) Kamimura, A.; Omata, Y.; Mitsudera, H.; Kakehi, A. J. Chem. Soc., Perkin Trans. 1 2000, 4499.
9. (a) Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1994, 67, 2514.
10. (b) Molander, G. A.; Andrews, S. W. Tetrahedron Lett. 1986, 27, 3115.
11. (c) Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453.
12. (a) Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron 1993, 49, 11169.
13. (b) Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1985, 107, 8294.
14. (c) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5405.
15. (d) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5415.
16. (e) Fujita, M.; Hiyama, T. Org. Synth. 1990, 69, 44.
17. (f) Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1991, 32, 6147.
18. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191.
19. Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem.-Eur. J. 1997, 3, 1941.
20. Bartoli, G.; Bosco, M.; Di Martino, E.; Marcantoni, E.; Sambri, L. Eur. J. Org. Chem. 2001, 2901.
21. The proton abstraction in 4A is expected to be difficult due to stereoelectronic factors (H in pseudo equatorial position): Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry, Vol. 1; Pergamon: New York, 1983, 274.
22. Bartoli, G.; Marcantoni, E.; Sambri, L. In Seminars in Organic Synthesis: XXV Summer School 'A. Corbella' 12-16/6/2000, Gargnano; Società Chimica Italiana: Camerino, 2000, 117-138.
23. (a) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: New York, 1994, 68.
24. (b) Imamoto, T. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I.; Schreiber, S. L., Eds.; Pergamon: London, 1991, Chap. 1.8.
25. Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L. Tetrahedron Lett. 2001, 42, 6093.
26. Bartoli, G.; Bellucci, M. C.; Bosco, M.; Marcantoni, E.; Sambri, L. Chem.-Eur. J. 1998, 4, 2154.
27. Cooper, G. D.; Finkbeiner, H. L. J. Org. Chem. 1962, 27, 1493.
28. Reetz, M. T. Organometallics in Synthesis, A Manual; Schlosser, M., Ed.; 1994, 195.
29. Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L. Tetrahedron Lett. 2001, 42, 8811.
30. 2S) to closely related systems.
31. (b) For the reduction of β-keto sulfones, see: Bartoli, G.; Bosco, M.; Cingolani, S.; Marcantoni, E.; Sambri, L. J. Org. Chem. 1998, 63, 3624.
32. (c) For the reduction of β-keto esters, see: Bartoli, G.; Bellucci, M. C.; Alessandrini, S.; Malavolta, M.; Marcantoni, E.; Sambri, L.; Dalpozzo, R. J. Org. Chem. 1999, 64, 1986.
33. (d) For the reduction of α-nitroketones, see: Ballini, R.; Bosica, G.; Marcantoni, E.; Vita, P.; Bartoli, G. J. Org. Chem. 2000, 65, 5854.
34. (e) For the reduction of β-keto carbonitriles, see: Bartoli, G.; Bosco, M.; Dalpozzo, R.; De Nino, A.; Procopio, A.; Sambri, L.; Tagarelli, A. Eur. J. Org. Chem. 2001, 2971.