Asymmetric synthesis of oxygen heterocycles via Pd-catalyzed dynamic kinetic asymmetric transformations: Application to nucleosides

Chemistry - A European Journal

Volumn 9, Issue 18, 2003, Pages 4442-4451

  Trost, Barry M ^a   Brown, Brian S ^a   McEachern, Ernest J ^a   Kuhn, Oliver ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Metathesis; Nucleosides; Palladium

Indexed keywords

CATALYSIS; CATALYSTS; ORGANIC COMPOUNDS; PALLADIUM;

ENANTIOSELECTIVITY;

OXYGEN;

HETEROCYCLIC COMPOUND; NUCLEOSIDE; OXYGEN DERIVATIVE; PALLADIUM; RUTHENIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; ISOMERISM; KINETICS; MODEL; RING CLOSING METATHESIS;

ALCOHOLS; CATALYSIS; CYCLIZATION; EPOXY COMPOUNDS; HETEROCYCLIC COMPOUNDS; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NUCLEOSIDES; ORGANOMETALLIC COMPOUNDS; OXYGEN; PALLADIUM; RUTHENIUM; STEREOISOMERISM;

EID: 0141645230     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304949     Document Type: Article

References (40)

1. L. A. Agrofoglio, S. R. Challand, Acyclic, Carbocyclic, and L-Nucleosides, Kluwer Academic Publishers, Dordrecht, 1998; for a recent review on synthesis see H. Vorbrüggen, C. Ruh-Pohlenz, Org. React. 2000, 55, 1.
2. L. A. Agrofoglio, S. R. Challand, Acyclic, Carbocyclic, and L-Nucleosides, Kluwer Academic Publishers, Dordrecht, 1998; for a recent review on synthesis see H. Vorbrüggen, C. Ruh-Pohlenz, Org. React. 2000, 55, 1.
3. P. Rajagopalan, F. D. Boudinot, C. K. Chu, B. C. Tennant, B. H. Baldwin, R. F. Schinazi, Antimicrob. Agents Chemother. 1996, 40, 642.
4. G. Gosselin, V. Boudou, J.-F. Griffon, G. Pavia, C. Pierra, J.-L. Imbach, A.-M. Auberin, R. F. Schinazi, A. Faraj, J.-P. Sommadossi, Nucleosides Nucleotides 1997, 16, 1389.
5. B. M. Trost, Z. Shi, J. Am. Chem. Soc. 1996, 118, 3037.
6. K. Kitano, H. Machida, S. Miura, Bioorg. Med. Chem. Lett. 1999, 9, 827.
7. T. Waga, H. Ohrui, H. Meguro, Nucleosides Nucleotides 1996, 15, 287.
8. I. Sugimoto, S. Shuto, S. Mori, S. Shigeta, A. Matsuda, Bioorg. Med. Chem. Lett. 1999, 9, 385.
9. a) M. E. Jung, A. Toyota, J. Org. Chem. 2001, 66, 2624;
10. b) G. H. Jones, M. Taniguchi, D. Tegg, J. G. Moffatt, J. Org. Chem. 1979, 44, 1309.
11. ′,5′-Didehydro: K. Haraguchi, H. Tanaka, T. Miyasaka, Tetrahedron Lett. 1990, 31, 227; ′,4′-didehydro: K. Haraguchi, H. Tanaka, U. Itoh, K. Yamaguchi, T. Miyasaka, J. Org. Chem. 1996, 61, 851.
12. ′,5′-Didehydro: K. Haraguchi, H. Tanaka, T. Miyasaka, Tetrahedron Lett. 1990, 31, 227; ′,4′-didehydro: K. Haraguchi, H. Tanaka, U. Itoh, K. Yamaguchi, T. Miyasaka, J. Org. Chem. 1996, 61, 851.
13. B. M. Trost, E. J. McEachern, F. D. Toste, J. Am. Chem. Soc. 1998, 120, 12702.
14. M. David, J. Saleau, A. Saleau, Bull. Soc. Chim. Fr. 1993, 130, 527.
15. B. M. Trost, F. D. Toste, J. Org. Chem. 1999, 64, 4545.
16. S.-T. Chen, J.-M. Fang, J. Org. Chem. 1997, 62, 4349.
17. For review see T. M. Tmka, R. M. Grubbs, Acc. Chem. Res. 2001, 34, 18; A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012; M. Jorgensen, P. Hadwiger, R. Madsen, A. E. Stütz, T. M. Wrodnigg, Curr. Org. Chem. 2000, 4, 565.
18. For review see T. M. Tmka, R. M. Grubbs, Acc. Chem. Res. 2001, 34, 18; A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012; M. Jorgensen, P. Hadwiger, R. Madsen, A. E. Stütz, T. M. Wrodnigg, Curr. Org. Chem. 2000, 4, 565.
19. For review see T. M. Tmka, R. M. Grubbs, Acc. Chem. Res. 2001, 34, 18; A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012; M. Jorgensen, P. Hadwiger, R. Madsen, A. E. Stütz, T. M. Wrodnigg, Curr. Org. Chem. 2000, 4, 565.
20. For review see T. M. Tmka, R. M. Grubbs, Acc. Chem. Res. 2001, 34, 18; A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012; M. Jorgensen, P. Hadwiger, R. Madsen, A. E. Stütz, T. M. Wrodnigg, Curr. Org. Chem. 2000, 4, 565.
21. A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130.
22. K. Hammer, C. Romming, K. Undheim, Tetrahedron 1998, 54, 10837; M. T. Crimmins, A. T. Choy, J. Am. Chem. Soc. 1999, 121, 5653.
23. K. Hammer, C. Romming, K. Undheim, Tetrahedron 1998, 54, 10837; M. T. Crimmins, A. T. Choy, J. Am. Chem. Soc. 1999, 121, 5653.
24. B. Rickborn, R. P. Thummel, J. Org. Chem. 1971, 36, 1365; C. L. Kissel, B. Rickborn, J. Org. Chem. 1972, 37 2060.
25. B. Rickborn, R. P. Thummel, J. Org. Chem. 1971, 36, 1365; C. L. Kissel, B. Rickborn, J. Org. Chem. 1972, 37 2060.
26. Y. Diaz, A. El-Laghdach, I. Matheu, S. Castillon, J. Org. Chem. 1997, 62, 1501.
27. a) H. Matsuhashi, H. Hattori, K. Tanabe, Chem. Lett. 1981, 341;
28. b) R. Paul, M. Fluchaire, G. Collardeau, Bull. Soc. Chim. Fr. 1950, 17, 668.
29. a) H. Wakamatsu, M. Nishida, N. Acachi, M. Mori, J. Org. Chem. 2001, 65, 3966;
30. b) D. P. Curran, P. B. Jacobs, R. L. Elliott, B. H. Kim, J. Am. Chem. Soc. 1987, 109, 5280.
31. B. M. Trost, X. Ariza, J. Am. Chem. Soc. 1999, 121, 10727.
32. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
33. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
34. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
35. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
36. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
37. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
38. During the course of these studies, similar metatheses were performed, see T. K. Maishal, D. K. Sinha-Mahapatra, K. Paranjape, A. Sarkar, Tetrahedron Lett. 2002, 43, 2263; for some examples of the synthesis of 5-, 6-, or 7-membered ring oxygen heterocyles, see G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 5426; C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354; R. J. Davoille, D. T. Rutherford, S. D. R. Christie, Tetrahedron Lett. 2000, 41, 1255; A. Briot, M. Biyard, V. Gouverneur, S. P. Nolan, C. Mioskowski, Org. Lett. 2000, 2, 1517; K. R. K. Prasad, D. Hoppe, Synlett 2000, 1067; M. T. Crimmins, A. L. Choy, J. Org. Chem. 1997, 62, 7548.
39. J. A. Adams, N. M. Heron, A. M. Koss, A. H. Hoveyda, J. Org. Chem. 1999, 64, 854.
40. For an alternative atom economic approach, see F. E. McDonald, C. B. Connolly, M. M. Gleason, T. B. Towne, K. D. Treiber, J. Org. Chem. 1993, 58, 6952.