Stereoselective three-carbon and two-carbon elongation of the carbon chain in N-Boc-protected α-aminoacylsilanes: An entry to functionalized β- amino alcohols and to statine analogues

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 8008-8013

  Bonini, Bianca Flavia ^a   Comes Franchini, Mauro ^a   Fochi, Mariafrancesca ^a   Laboroi, Fréderic ^b   Mazzanti, Germana ^a   Ricci, Alfredo ^a   Varchi, Greta ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b 5 Mail Gay Lussac   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; ISOLEUCINE; PHENYLALANINE; SILANE DERIVATIVE; STATINE DERIVATIVE;

ALKYLATION; ARTICLE; POLYMERIZATION; REACTION ANALYSIS; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032740861     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982501x     Document Type: Article

References (54)

1. (a) Jurczak, J.; Gobielowsky, A. Chem. Rev. 1989, 89, 149-164.
2. (b) Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370-4382.
3. (c) Huff, J. R. J. Med. Chem. 1991, 34, 2305-2314.
4. (d) Reetz, M. T.; Kanand, J.; Griebenow, N.; Harms, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1626-1629 and references therein.
5. (e) Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570-6571.
6. Nicolau, K. C., Dai, W.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44.
7. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
8. (b) Ajer, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. (Washington D. C.) 1996, 96, 835-875.
9. (c) Shen, Z. X.; Lu, J.; Zhang, Q.; Zhang, Y. W. Tetrahedron: Asymmetry 1997, 8, 2287-2289.
10. (d) Wilken, J.; Kossenjans, M.; Groger, H.; Martens, J. Ibid. 1997, 8, 2007-2015.
11. (e) Trentmann, W.; Mehler, T.; Martens, J. Ibid. 1997, 8, 2033-2043.
12. (f) Andres, M.; Martin, Y.; Pedrosa, A.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787-3794.
13. (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546.
14. (b) D'Aniello, F.; Mann, A.; Matii, M.; Taddei, M. J. Org. Chem. 1994, 59, 3762-3768 and references therein.
15. (c) Dondoni, A.; Perrone, D.; Merino, P. J. Org. Chem. 1995, 60, 8074-8080.
16. Gryko, D.; Urbanczyk-Lipkowska, Z.; Jurczak, J. Tetrahedron: Asymmetry 1997, 24, 4059-4067.
17. (a) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1988, 110, 4826-4827.
18. (b) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1994, 35, 741-744.
19. Bonini, B. F.; Comes-Franchini, M.; Mazzanti, G.; Ricci, A.; Sala, M. J. Org. Chem. 1996, 61, 7242-7243.
20. Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Gawronsky, J.; Mazzanti, G.; Ricci, A.; Varchi, G. Eur. J. Org. Chem. 1999, 437-445.
21. Kocienski, P. J. In Protecting Groups; Georg Thieme Verlag: Stuttgart, New York, 1994; Chapter 6, pp 192-195.
22. Carpino, L. A.; Beyermann, M.; Wenschuh, H.; Bienert, M. Acc. Chem. Res. 1996, 29, 268-274.
23. (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
24. (b) Levin, I. J.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993.
25. (a) Mitchell, R. H.; Iyer, V. S. Tetrahedron Lett. 1993, 34, 3683-3686.
26. (b) Nimitz, J. S.; Mosher, H. S. J. Org. Chem. 1981, 46, 211-213.
27. (c) Bhattacharya, A.; Williams, J. M.; Amato, J. S.; Dolling, U. H.; Grabowsky, E. J. J. Synth. Commun. 1990, 30, 2683-2690.
28. Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A.; Varchi, G. Synlett 1998, 1013-1015.
29. (a) Dondoni, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; p 377.
30. (b) Jurzac, J.; Golebiowsky, A. In Antibiotics and Antiviral Compounds. Chemical Synthesis and Modification; Kroh, K., Kirst, H., Maag, H., Eds.; VCH: Weinheim 1993; p 343.
31. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 16, 1295-1298.
32. Kobayashi, S. Synlett 1994, 689-701, and references therein.
33. Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181-1192.
34. 13C NMR spectra of the crude. Moreover, in the case of 5, the optical purity of the amino alcohols 9a and 9b was proved by converting them into the corresponding Mosher esters. On these grounds, significant racemization in 5 and 6 could be ruled out.
35. Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1982, 104, 6809-6811.
36. (a) Futagawa, S.; Inui, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308-3310.
37. (b) Wagner, B.; Buegelmans, R., Zhu, J. Tetrahedron Lett. 1996, 37, 6557-6560.
38. (c) Laïb, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709-1713.
39. Paquette, L.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293-4301.
40. (a) Santelli, M.; Pons, J.-M. In Lewis Acids and Selectivity in Organic Synthesis; CRC Press: New York, 1996; p 135.
41. (b) Reetz, M. T,; Kessler, K.; Yung, A. Tetrahedron Lett. 1984, 25, 729-732.
42. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-30.
43. For phenylalanine: (a) Parkes, K.; Bushnell, D.; Crackett, P.; Dunsdon, S. J. Org. Chem. 1994, 59, 3656-3664.
44. (b) Holmes, D. S.; Bethell, R. C.; Commack, N.; Clemens, I. R.; Kitchin, J.; McMeekin, P.; Mo, C. L.; Orr, D. C.; Patel, B.; Paternoster, I. L.; Storer, R. J. Med. Chem. 1993, 36, 3129-3136.
45. (c) Nishi, T.; Morisawa, Y. Heterocycles 1989, 29, 1835-1842.
46. For isoleucine: (d) Rinehart, L.; Sakai, R.; Kishore, V.; Sullins, D. W., Li, K. J. Org. Chem. 1992, 57, 3007-3013.
47. (e) Hamada, Y.; Kondo, Y.; Shibata, M.; Shioiri, T. J. Am. Chem. Soc. 1989, 111, 669-673.
48. Takemoto, Y.; Matsumoto T.; Ito, Y.; Terashima, S. Tetrahedron Lett. 1990, 31, 217-218.
49. (a) Harris, B. D.; Bhat, K. L.; Jouillè, M. M. Tetrahedron. Lett. 1987, 25, 2837-2840.
50. (b) Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 869-873.
51. (c) Kessler, H.; Schudok, M. Synthesis 1990, 457-458.
52. Hoffmann, R. V.; Tao, J. J. Org. Chem. 1997, 62, 2292-2297.
53. (a) Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. 1 1981, 2527.
54. (b) Harwood: L. M.; Moodie, C. J. Organocopper Reagents; Taylor, J. K., Ed.; Oxford University Press: New York, 1994; pp 260-261.