Ring-closing metathesis of allylic O,O- and N,O-acetals

Advanced Synthesis and Catalysis

Volumn 344, Issue 6-7, 2002, Pages 736-748

  Kinderman, Sape S ^a   Doodeman, Robin ^a   Van Beijma, Jetze W ^a   Russcher, Jaap C ^b   Tjen, Kim C M F ^a   Kooistra, T Martijn ^a   Mohaselzadeh, Homayun ^a   Van Maarseveen, Jan H ^a   Hiemstra, Henk ^a   Schoemaker, Hans E ^a,c   Rutjes, Floris P J T ^a,b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^c DSM RESEARCH   (Netherlands)

Author keywords

Allylic N,O acetals; Allylic O,O acetals; Amidopalladation; Oxypalladation; Ring closing metathesis

Indexed keywords

EID: 0011931581     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/1615-4169(200208)344:6/7<736::AID-ADSC736>3.0.CO;2-8     Document Type: Article

References (58)

1. For review articles, see: a) A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012;
2. b) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18;
3. c) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413.
4. d) A. Fürstner, Top. Organomet. Chem. 1998, 1, 37.
5. For several investigations into new RCM catalysts, see: a) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2674;
6. b) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247;
7. c) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953;
8. d) S. S. Zhu, D. R. Cefalo, D. S. La, J. Y. Jamieson, W. M. Davis, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 1999, 121, 8251;
9. e) G. S. Wheaterhead, J. G. Ford, E. J. Alexanian, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 1828;
10. f) A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236.
11. a) F. P. J. T. Rutjes, T. M. Kooistra, H. Hiemstra, H. E. Schoemaker, Synlett 1998, 192;
12. b) M. T. Crimmins, B. W. King, J. Am. Chem. Soc. 1998, 120, 9084;
13. c) H. Ovaa, M. A. Leeuwenburgh, H. S. Overkleeft, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 3025;
14. d) P. A. V. van Hooft, M. A. Leeuwenburgh, H. S. Overkleeft, G. A. van der Marel, C. A. A. van Boeckel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 6061;
15. e) M. Scholl, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 1425;
16. f) M. J. Bassindale, P. Hamley, A. Leitner, J. P. A. Harrity, Tetrahedron Lett. 1999, 40, 3247;
17. g) K. C. M. F. Tjen, S. S. Kinderman, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Chem. Commun. 2000, 699;
18. h) R. Doodeman, F. P. J. T. Rutjes, H. Hiemstra, Tetrahedron Lett. 2000, 41, 5979;
19. i) J. Mulzer, M. Hanbauer, Tetrahedron Lett. 2000, 41, 33.
20. For a silicon tethered example, see: T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429 and references cited therein.
21. Some recent selected examples on dihydropyrans: a) B. Schmidt, H. Wildemann, Eur. J. Org. Chem. 2000, 3145;
22. b) A. K. Ghosh, H. Lei, J. Org. Chem. 2000, 65, 4779;
23. c) D. P. Steinhuebel, J. J. Fleming, J. Du Bois, Org. Lett. 2002, 4, 293;
24. d) T. B. Durham, M. J. Miller, Org. Lett. 2002, 4, 135.
25. For examples on tetrahydropyridines and azepines, see: e) J. Åhman, P. Somfai, Tetrahedron Lett. 1995, 36, 303;
26. f) S. N. Osipov, N. M. Kobelikova, G. T. Shchetnikov, A. F. Kolomiets, C. Bruneau, P. H. Dixneuf, Synlett 2001, 621;
27. g) W. H. Pearson, A. Aponick, Org. Lett. 2001, 3, 1327.
28. For examples on chromenes, see: h) B. M. Trost, F. D. J. Toste, J. Am. Chem. Soc. 1998, 120, 9074.
29. i) K. S. Atwal, G. J. Grover, F. N. Ferrara, S. Z. Ahmd, P. G. Sleph, S. Dzwonczyk, D. E. Normandin, J. Med. Chem. 1995, 38, 1966.
30. For examples, see: a) S. A. Angle, J. G. Breitenbucher, Tetrahedron Lett. 1993, 34, 3985;
31. b) T. Hamada, T. Zenkoh, H. Sato, O. Yonemitsu, Tetrahedron Lett. 1991, 32, 1649;
32. c) T. Bauer, C. Chapuis, A. Jezewski, J. Kozak, J. Jurczak, Tetrahedron: Asymmetry 1996, 7, 1391;
33. d) T. Bauer, A. Jezewski, J. Jurczak, Tetrahedron: Asymmetry 1996, 7, 1405;
34. e) M. Terada, K. Mikami, T. Nakai, Tetrahedron Lett. 1991, 32, 935.
35. The dihydropyran as a useful building block in the total synthesis of fostriecin (CI-920): f) D. L. Boger, S. Ichikawa, W. Zhong, J. Am. Chem. Soc. 2001, 125, 4161.
36. a) G. C. Fu, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1993, 115, 9856;
37. b) A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson, M. R. Giles, E. L. Marshall, P. A. Procopiou, A. J. P. White, D. J. Williams, J. Org. Chem. 1998, 63, 7893.
38. For an entry into applications of the strongly related N-acyliminium ion intermediates, see: W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817.
39. A detailed account on mechanistic aspects of Pd-mediated coupling reactions of alkoxyallenes with amines and alcohols will be published in the near future.
40. For a discussion on metathesis cyclizations of vinylglycine-derived substrates, see: J.-M. Campagne, L. Ghosez, Tetrahedron Lett. 1998, 39, 6175.
41. a) L. B. Wolf, T. Sonke, K. C. M. F. Tjen, B. Kaptein, Q. B. Broxterman, H. E. Schoemaker, F. P. J. T. Rutjes, Adv. Synth. Catal. 2001, 343, 662;
42. b) T. Sonke, B. Kaptein, W. H. J. Boesten, Q. B. Broxterman, J. Kamphuis, F. Formaggio, C. Toniolo, F. P. J. T. Rutjes, H. E. Schoemaker, in Stereoselective Biocatalysis, (Ed.: R. N. Patel), Marcel Dekker, New York, 2000, pp. 23-59.
43. For examples of formation of sulfonyl-protected N,O-acetals, see e. g.: a) T. Shono, Y. Matsumura, S. Katoh, K. Takeuchi, K. Sasaki, T. Kamada, R. Shimizu, J. Am. Chem. Soc. 1990, 112, 2368;
44. b) R. Consonni, P. D. Croce, R. Ferraccioli, J. Heterocycl. Chem. 1990, 27, 427.
45. For recent examples of Pd-catalyzed allylic O,O-acetal formation and subsequent functionalization in natural product synthesis, see e. g.: a) C. Held, R. Fröhlich, P. Metz, Angew. Chem. Int. Ed. 2001, 40, 1058;
46. b) G. T. Nadolski, B. S. Davidson, Tetrahedron Lett. 2001, 42, 797.
47. For alternative metathesis approaches towards substituted chromenes, see e. g.: a) S. Chang, R. H. Grubbs, J. Org. Chem. 1998, 63, 864;
48. b) J. P. A. Harrity, D. S. La, D. R. Cefalo, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1998, 120, 2343;
49. c) P. Wipf, W. S. Weiner, J. Org. Chem. 1999, 64, 5321.
50. L. Brandsma, H. D. Verkruijsse, Synthesis of acetylenes, allenes and cumulenes, a laboratory manual, in Studies in Organic Chemistry, Vol. 8, Elsevier, Amsterdam, 1981.
51. S. D. Bull, S. G. Davies, S. W. Epstein, M. A. Leech, J. V. A. Ouzman, J. Chem. Soc. Perkin Trans. 1 1998, 2321.
52. Isolation: F. E. King, T. J. King and A. J. Warwick, J. Chem. Soc. 1950, 3590.
53. For other recent enantiopure syntheses of baikiain, see: a) X. Ginesta, M. A. Pericàs, A. Riera, Tetrahedron Lett. 2002, 43, 779;
54. b) G. Guillena, C. Nâjera, J. Org. Chem. 2000, 65, 7310;
55. c) A. Mazon, C. Nájera, Tetrahedron: Asymmetry 1997, 11, 1855.
56. Such a high diastereoselectivity has been observed in comparable systems without the unsaturation: C. Yang, Y. Xu, L. Liao, W. Zhou, Tetrahedron Lett. 1998, 39, 9228 and references cited therein.
57. For a highlight on methyl propadienyl ether: R. Pulz, Synlett 2000, 1697.
58. For a review on alkoxy-1,2-propadienes, see: R. Zimmer, Synthesis 1993, 167.