Highly efficient synthesis of azabicyclo[x.y.0]alkane amino acids and congeners by means of Rh-catalyzed cyclohydrocarbonylation

Journal of Organic Chemistry

Volumn 72, Issue 6, 2007, Pages 1871-1882

  Chiou, Wen Hua ^a   Mizutani, Nobihiro ^a   Ojima, Iwao ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYST ACTIVITY; CYCLIZATION; PARAFFINS; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

CONGENERS; CYCLOHYDROCARBONYLATION; DIASTEREOSELECTIVITY; INTRAMOLECULAR CONDENSATION;

AMINO ACIDS;

ALKANE DERIVATIVE; AMINO ACID DERIVATIVE; BICYCLO COMPOUND; RHODIUM;

ADDITION REACTION; AMINO ACID SYNTHESIS; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY;

ALKANES; AMINO ACIDS; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; HYDROCARBONS, CYCLIC; RHODIUM;

EID: 33947233410     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061692y     Document Type: Article

References (42)

1. Cluzeau, J.; Lubell, W. D. Pept. Sci. 2005, 80, 98-150.
2. Maison, W.; Prenzel, A. H. G. P. Synthesis 2005, 1031-1048.
3. Hanessian, S.; Laoui, B. R. Bioorg. Med. Chem. Lett. 1994, 4, 1397-1400.
4. Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783.
5. Gramberg, D.; Robinson, J. A. Tetrahedron Lett. 1994, 35, 861-864.
6. Sato, K.; Nagai, U. J. Chem. Soc., Perkin Trans. 1 1986, 1231-1234.
7. Haubner, R.; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881-7891.
8. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
9. Falorni, M.; Giacomelli, G.; Nieddu, F.; Taddei, M. Tetrahedron Lett. 1997, 38, 4663-4666.
10. Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Brown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
11. Robl, J. A.; Sun, C.-Q.; Stevenson, J.; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577.
12. Fink, C. A.; Carlson, J. E.; McTaggart, P. A.; Qiao, Y.; Webb, R.; Chatelain, R.; Jeng, A. Y.; Trapani, A. J. J. Med. Chem. 1996, 39, 3158-3168.
13. Flynn, G. A. PCT Int. Appl. WO 9410193 A1, 1994.
14. Tamura, S. Y.; Goldman, E. A.; Brunck, T. K.; Ripka, W. C.; Semple, J. E. Bioorg. Med. Chem. Lett. 1997, 7, 331-336.
15. Wagner, J.; Kallen, J.; Ehrhardt, C.; Evenou, J.-P.; Wagner, D. J. Med. Chem. 1998, 41, 3664-3674.
16. Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650.
17. Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577-3592.
18. Siddiqui, M. A.; Préville, P.; Tarazi, M.; Warder, S. E.; Eby, P.; Gorseth, E.; Puumala, K.; DiMaio, J. Tetrahedron Lett. 1997, 38, 8807-8810.
19. Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.
20. Estiarte, M. A.; Rubiralta, M.; Diez, A. J. Org. Chem. 2000, 65, 6992-6999.
21. Robl, J. A. Tetrahedron Lett. 1994, 35, 393-396.
22. Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 11, 935-936.
23. Mizutani, N.; Chiou, W.-H.; Ojima, I. Org. Lett. 2002, 4, 4575-4578.
24. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992.
25. Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 909-917.
26. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204.
27. Ojima, I.; Korda, A.; Shay, W. R. J. Org. Chem. 1991, 56, 2024-2030.
28. Ojima, I.; Tzamarioudaki, M.; Eguchi, M. J. Org. Chem. 1995, 60, 7078-7079.
29. Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
30. Ojima, I.; Iula, D. M.; Tzamarioudaki, M. Tetrahedron Lett. 1998, 39, 4599-4602.
31. Ojima, I. Pure Appl. Chem. 2002, 74, 159-166.
32. Ojima, I.; Bonafoux, D.; Lee, S.-Y. In Encyclopedia of Catalysis; Horvath, I. T., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2003; Vol. 2, pp 706-766.
33. Campi, E. M.; Jackson, W. R.; McCubbin, Q. J.; Trnacek, A. E. Aust. J. Chem. 1994, 47, 1061-1071.
34. Billig, E.; Abatjoglou, A. G.; Bryant, D. Union Carbide, US 476498, 1988.
35. Otsuka, M.; Kittaka, A.; Iimori, T.; Yamashita, H.; Kobayashi, S.; Ohno, M. Chem. Pharm. Bull. 1985, 33, 509.
36. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 1, 31-33.
37. Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry, Peraamon: New York, 1983, Chapter 6.
38. Johnson, F. Chem. Rev. 1968, 68, 375-413.
39. Booth, H.; Everett, J. R. J. Chem. Soc., Chem. Commun. 1976, 8, 278-279.
40. Booth, H. E.; Jeremy R. J. Chem. Soc., Perkin Trans. 2 1980, 2, 255-259.
41. Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Thomson Publishing Inc.: 1998, p 138.
42. Baldwin reported the strong directing effect of the Boc-(S)-serine residue on the selective formation of the 65 bridgehead configuration in his tandem ozonolysis-cyclization of Boc-(S)-Ser-(S/R)-(homoallyl)Gly- OBn substrates, which gave the corresponding (6S)-1-aza-5-oxobicyclo-[4. 3.0] product in 72-77% yield with high diastereoselectivity (6S:6R = > 7:1) regardless of the absolute configuration of the homoallylglycine residue (see ref 22). Marshall also reported a similar directing effect of Boc-(S)-homoserine residue in his electrochemical (i.e., anodic electrolysis) cyclization of Boc-(S)-homo-Ser-(S/R)-Pro-OMe, which gave (7S)-1-aza-6-oxabicyclo[5.3.0] product exclusively, regardless of the absolute configuration of the proline residue although the chemical yields were only moderate (48-52%) (see ref 26).