Diastereoselective reduction of a chiral N-Boc-protected δ-amino-α,β-unsaturated γ-keto ester Phe-Gly dipeptidomimetic

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9186-9191

  Våbenø, Jon ^a   Brisander, Magnus ^a   Lejon, Tore ^a   Luthman, Kristina ^a,b  

^a UNIVERSITY OF TROMSØ   (Norway)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHELATION; ESTERS; REDUCTION;

FELKIN ANH CONTROL;

CATALYST SELECTIVITY;

ALCOHOL; ALUMINUM DERIVATIVE; BORON DERIVATIVE; ESTER DERIVATIVE; GLYCINE DERIVATIVE; LITHIUM DERIVATIVE; PHENYLALANINE DERIVATIVE;

ARTICLE; CHELATION; CHIRALITY; REDUCTION;

ALUMINUM; AMINO ALCOHOLS; BORON; CHELATING AGENTS; DIPEPTIDES; HEXANOIC ACIDS; INDICATORS AND REAGENTS; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; REDUCING AGENTS; STEREOISOMERISM;

EID: 0347367042     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020442o     Document Type: Article

References (50)

1. Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576.
2. For a review on preparation and reactions of α-amino aldehydes, ketones, aldimines, and ketimines, see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-46.
3. For a review of diastereoselective synthesis of amino alcohols from chiral amino carbonyl compounds in general, see: Tramontini, M. Synthesis 1982, 8, 605-644.
4. Hashiguchi, S.; Kawada, A.; Natsugari, H. Synthesis 1992, 403-408.
5. Raddatz, P.; Radunz, H. E.; Schneider, G.; Schwartz, H. Angew. Chem. 1988, 100, 414-15.
6. Dufour, M. N.; Jouin, P.; Poncet, J.; Pantaloni, A.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1986, 11, 1895-9.
7. Harris, B. D.; Joullie, M. M. Tetrahedron 1988, 44, 3489-3500.
8. Maugras, I.; Poncet, J.; Jouin, P. Tetrahedron 1990, 46, 2807-2816.
9. Reductions of the methyl ester (see ref 10) and ethyl ester (see ref 16) derivatives have been described previously.
10. Berts, W.; Luthman, K. Tetrahedron 1999, 55, 13819-13830.
11. Jenmalm, A.; Berts, W.; Li, Y. L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139-1148.
12. Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1995, 60, 1026-1032.
13. The alcohols can be obtained also from ring opening of the corresponding epoxides; see ref 11 and references therein.
14. Kaltenbronn, J. S.; Hudspeth, J. P.; Lunney, E. A.; Michniewicz, B. M.; Nicolaides, E. D.; Repine, J. T.; Roark, W. H.; Stier, M. A.; Tinney, F. J.; Woo, P. K. W.; Essenburg, A. D. J. Med. Chem. 1990, 33, 838-845.
15. Urban, J.; Konvalinka, J.; Stehlikova, J.; Gregorova, E.; Majer, P.; Soucek, M.; Andreansky, M.; Fabry, M.; Strop, P. FEBS Lett. 1992, 298, 9-13.
16. Litera, J.; Budesinsky, M.; Urban, J.; Soucek, M. Collect. Czech. Chem. Commun. 1998, 63, 231-244.
17. Benedetti, F.; Miertus, S.; Norbedo, S.; Tossi, A.; Zlatoidzky, P. J. Org. Chem. 1997, 62, 9348-9353.
18. For a summary, see: Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 876-880.
19. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199-2204.
20. Cherest, M.; Felkin, H. Tetrahedron Lett. 1968, 9, 2205-2208.
21. For an overview of reduction of carbonyl groups with metal hydrides, see: Greeves, N. In Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry. Volume 8: Reduction, 1st Ed.; Trost, B. M., Fleming, I., Eds.; Pergamon Press: 1991; Vol. 8, p 1-24, and references therein.
22. large in the Felkin-Anh model, as shown in Figure 1.
23. Sengupta, S.; SenSarma, D. Tetrahedron: Asymmetry 1999, 10, 4633-4637.
24. Sengupta, S.; SenSarma, D. Tetrahedron Lett. 2001, 42, 485-487.
25. Tao, J. H.; Hoffman, R. V. J. Org. Chem. 1997, 62, 6240-6244.
26. 4 in EtOH and with L-Selectride in THF (Rotella, D. P. Tetrahedron Lett, 1995, 36, 5453-5456).
27. 4 in EtOH and with L-Selectride in THF (Rotella, D. P. Tetrahedron Lett, 1995, 36, 5453-5456).
28. 4 in EtOH and with L-Selectride in THF (Rotella, D. P. Tetrahedron Lett, 1995, 36, 5453-5456).
29. Deziel, R.; Plante, R.; Caron, V.; Grenier, L.; LlinasBrunet, M.; Duceppe, J. S.; Malenfant, E.; Moss, N. J. Org. Chem. 1996, 61, 2901-2903.
30. Kim, B. H.; Chung, Y, J.; Ahn, H. J.; Ha, T. K. Bull. Korean Chem. Soc. 1996, 17, 401-404.
31. Saiah, M. K. E.; Pellicciari, R. Tetrahedron Lett. 1995, 36, 4497-4500.
32. Darkins, P.; McCarthy, N.; McKervey, M. A.; Ye, T. J. Chem. Soc., Chem. Commun. 1993, 1222-1223.
33. The tert-butyl glyoxylate was synthesized via an oxidative cleavage ofdi-tert-butyl tartrate, which was obtained by esterification of L-tartaric acid with a tert-butyl dicyclohexyl isourea derivative according to ref 45. See also the Experimental Section.
34. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
35. Since successful enzymatic reductions of N-protected γ-amino-β-keto esters using microorganisms have been reported (see refs 4 and 5), we tried both baker's yeast and Pichia anomala (also known as Hansenula anomala) in reductions of 1. However, both reactions failed, as no alcohol product could be detected by NMR spectroscopy, probably as a result of the nonfavored distance between the two keto ester carbonyl groups in 1. Therefore, this route to alcohols 2 and 3 was not further explored.
36. Sengupta, S.; Das, D.; Mondal, S. Synlett 2001, 1464-1466.
37. 4 according to ref 48.
38. For a review of enantioselective reduction of ketones, including oxazaborolidines, see: Singh, V. K. Synthesis 1992, 605-617, and references therein.
39. Umino, N.; Iwakuma, T.; Itoh, N. Chem. Pharm. Bull. 1979, 27, 1479-1481.
40. Itsuno, S.; Ito, K. J. Org. Chem. 1984, 49, 555-557.
41. Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2039-44.
42. Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045-1056.
43. 3 in THF at -5 °C on a substrate in which the N-carbamate protecting group had been replaced by the more sterically demanding N-trityl group to obtain Felkin-Anh control (the syn-isomer). However, in contrast to Hoffman et al., we wanted to use the same starting material for selective synthesis of both alcohol derivatives without changing protecting groups. Therefore we focused our efforts on finding reducing agents that favored the Felkin-Anh-controlled mechanism.
44. For a review of α-pinene-based borane reagents, including DIP-chloride and Alpine-Hydride, see: Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, 1-19, and references therein.
45. Midland, M. M.; Kazubski, A.; Woodling, R. E. J. Org. Chem. 1991, 56, 1068-1074.
46. Berts, W.; Luthman, K. Unpublished results.
47. Henry, R. A. J. Heterocycl. Chem. 1976, 13, 391-392.
48. Uray, G.; Lindner, W. Tetrahedron 1988, 44, 4357-4362.
49. Grinde, S. Master Thesis: Design og Syntese av Dipeptidomimetika som Ligand for Transportmolekylet PepT1; University of Tromsø: Tromsø, 1999.
50. Crabbé, P.; García, G. A.; Rius, C. J. Chem. Soc., Perkin Trans. 1 1973, 810-816.