Enantioselective syntheses of 2-substituted pyrrolidines from allylamines by domino hydroformylation-condensation: Short syntheses of (S)-nicotine and the alkaloid 225C

Synlett

Volumn , Issue 9, 2009, Pages 1413-1416

  Dübon, Pierre ^a   Farwick, Andreas ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkaloids; Cyclizations; Domino reactions; Hydroformylation; Pyrrolidines

Indexed keywords

ALKALOID DERIVATIVE; ALLYLAMINE DERIVATIVE; FUNCTIONAL GROUP; LIGAND; NICOTINE; NITROGEN; PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; HYDROFORMYLATION; POLYMERIZATION; RACEMIZATION; REDUCTION KINETICS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 67649380760     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217165     Document Type: Article

References (61)

1. (a) Helmchen, G. In Iridium Complexes in Organic Synthesis; Oro, L. A.; Claver, C., Eds.; Wiley-VCH: Weinheim, 2009, 211.
2. (b) Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675.
3. (c) Takeuchi, R.; Kezuka, S. Synthesis 2006, 3349.
4. (d) Miyabe, H.; Takemoto, Y. Synlett 2005, 1641.
5. (a) Streiff, S.; Welter, C.; Schelwies, M.; Lipowsky, G.; Miller, N.; Helmchen, G. Chem. Commun. 2005, 2957.
6. (b) Welter, C.; Moreno, R. M.; Streiff, S.; Helmchen, G. Org. Biomol. Chem. 2005, 3, 3266.
7. (c) Böhrsch, V.; Blechert, S. Chem. Commun. 2006, 1968.
8. Schelwies, M.; Dempwolff, A.; Rominger, F.; Helmchen, G. Angew. Chem. Int. Ed. 2007, 46, 5598;
9. Angew. Chem. 2007, 119, 5694.
10. (a) Allylamines prepared by Ir-catalyzed asymmetric allylic substitution have been used in hydroformylation-indolization sequences: Bondziæ, B. P.; Farwick, A.; Liebich, J.; Eilbracht, P. Org. Biomol. Chem. 2008, 3723.
11. (b) For preparation of an indolizine via hydroformylation of an N-allyl-pyrrole, see: Guazzelli, G.; Lazzaroni, R.; Settambolo, R. Beilstein J. Org. Chem. 2008, 4, 2.
12. For a review, see: (a) Eilbracht, P.; Schmidt, A. M. Top. Organomet. Chem. 2006, 18, 65.
13. (b) Eilbracht, P.; Bärfacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Roggenbruck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329.
14. (c) Ahmed, M.; Seayad, A. M.; Jackstell, R.; Beller, M. J. Am. Chem. Soc. 2003, 125, 10311.
15. (d) Ahmed, M.; Buch, C.; Routaboul, L.; Jackstell, R.; Klein, H.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2007, 13, 1594; and previous work cited there.
16. (a) Vieira, T. O.; Alper, H. Chem. Commun. 2007, 2710.
17. (b) Wittmann, K.; Wisniewski, W.; Mynott, R.; Leitner, W.; Kranemann, C. L.; Rische, T.; Eilbracht, P.; Sander, S.; Ernsting, J. M. Chem. Eur. J. 2001, 7, 4584.
18. (c) Eguchi, M.; Tzamarioudaki, M.; Ojima, I. J. Org. Chem. 1995, 60, 7078.
19. (d) Vidal, E. S.; Ojima, I. J. Org. Chem. 1998, 63, 7999.
20. (e) Spangenberg, T.; Airiau, E.; Bui The Thuong, M.; Donnard, M.; Billet, M.; Mann, A. Synlett 2008, 2859.
21. (f) Airiau, E.; Spangenberg, T.; Girard, N.; Schoenfelder, A.; Salvadori, J.; Taddei, M.; Mann, A. Chem. Eur. J. 2008, 14, 10938.
22. (g) Spangenberg, T.; Breit, B.; Mann, A. Org. Lett. 2009, 11, 261.
23. For leading references to asymmetric syntheses of pyrrolidines, including alkaloid 225C, see: Davis, F. A.; Xu, H.; Wu, Y.; Zhang, J. Org. Lett. 2006, 8, 2273.
24. Rhodium-Catalyzed Hydroformylation; van Leeuwen, P. W. N. M.; Claver, C., Eds.; Kluwer Academic: Dordrecht, 2000.
25. Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895.
26. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066.
27. (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164.
28. (b) Welter, C.; Dahnz, A.; Brunner, B.; Streiff, S.; Dübon, P.; Helmchen, G. Org. Lett. 2005, 7, 1239.
29. (c) Gnamm, C.; Franck, G.; Miller, N.; Stork, T.; Brödner, K.; Helmchen, G. Synthesis 2008, 3331.
30. Keränen, M. D.; Eilbracht, P. Org. Biomol. Chem. 2004, 2, 1688.
31. All new compounds described were fully characterized by elemental analysis and spectroscopic data. Yields always refer to isolated products.
32. 2.
33. For a review, see: (a) Felpin, F.-X.; Lebreton, A. Eur. J. Org. Chem. 2003, 3693.
34. (b) Wagner, F. F.; Comins, D. L. Tetrahedron 2007, 63, 8065.
35. (c) Schäfer, B. Chem. Unserer Zeit 2008, 42, 330.
36. (d) Baxendale, I. R.; Brusotti, G.; Matsuoka, M.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 143.
37. (e) Welter, C.; Moreno, R. M.; Streiff, S.; Helmchen, G. Org. Biomol. Chem. 2005, 3, 3266.
38. Very recently, a short synthesis of (S)-nicotine via hydroformylation of a homoallylazide has been reported, cf. ref. 6g.
39. Weihofen, R.; Tverskoy, O.; Helmchen, G. Angew. Chem. Int. Ed. 2006, 45, 5546;
40. Angew. Chem. 2006, 118, 5673.
41. Weihofen, R.; Dahnz, A.; Tverskoy, O.; Helmchen, G. Chem. Commun. 2005, 3541.
42. (a) Spiess, S.; Berthold, C.; Weihofen, R.; Helmchen, G. Org. Biol. Chem. 2007, 5, 2357.
43. (b) Pouy, M. J.; Leitner, A.; Weix, D. J.; Ueno, S.; Hartwig, J. F. Org. Lett. 2007, 9, 3949.
44. (c) Singh, O. V.; Han, H. Tetrahedron Lett. 2007, 48, 7094.
45. This has only been observed previously with derivatives of the parent allylamine using Ph3P as ligand, see: Dong, Y.; Busacca, C. A. Tetrahedron Lett. 1996, 37, 3947.
46. (a) Tissot-Croset, K.; Polet, D.; Gille, S.; Hawner, C.; Alexakis, A. Synthesis 2004, 2586.
47. (b) Polet, D.; Alexakis, A.; Tissot-Croset, K.; Corminboeuf, C.; Ditrich, K. Chem. Eur. J. 2006, 12, 3596.
48. We have found only one report on such a reaction, the hydroformylation of the parent allylamine, see: Lin, J. J.; Larkin, J. M.; Knifton, J. F. In Catalysis of Organic Reactions; Augustine, R. L., Ed.; Dekker: New York, 1988, 29.
49. For previous syntheses, see: (a) Pedder, D. J.; Fales, H. M.; Jaouni, T.; Blum, M.; MacConnell, J.; Crewe, R. M. Tetrahedron 1976, 32, 2275.
50. (b) Tufariello, J. J.; Puglis, J. M. Tetrahedron Lett. 1986, 27, 1489.
51. (c) Wistrand, L.-G.; Skinjar, M. Tetrahedron 1991, 47, 573.
52. (d) Oppolzer, W.; Bochet, C. G.; Merifield, E. Tetrahedron Lett. 1994, 35, 7015.
53. (e) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. Am. Chem. Soc. 1999, 121, 3633.
54. (a) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.
55. (b) Côtè, A.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 2771.
56. For a review, see: (a) Alvaro, G.; Savoia, D. Synlett 2002, 651.
57. (b) Yamada, H.; Kawate, T.; Nishida, A.; Nakagawa, M. J. Org. Chem. 1999, 64, 8821.
58. (c) Takemoto, Y.; Takeuchi, J.; Iwata, C. Tetrahedron Lett. 1993, 34, 6069.
59. (d) Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A.; Villa, M. Tetrahedron 1999, 55, 8103.
60. We used apparatus described in: Bartels, B.; Garcia-Yebra, C.; Helmchen, G. Eur. J. Org. Chem. 2003, 1097.
61. Our procedure complements Buchwald's similarly short asymmetric hydrogenation route: Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.