Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(Arylmethyl)- and 2-(Alkenylmethyl)pyrrolidines

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12157-12159

  Mai, Duy N ^a   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ARYL BROMIDES; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PYRROLIDINE DERIVATIVES; PYRROLIDINES;

BROMINE COMPOUNDS; CATALYSIS; ENANTIOMERS; OLEFINS;

PALLADIUM;

2 (ALKENYLMETHYL)PYRROLIDINE; 2 (ARYLMETHYL)PYRROLIDINE; PYRROLIDINE DERIVATIVE; TYLOPHORINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; BIOTRANSFORMATION; CHEMICAL REACTION; ENANTIOMER;

AMINATION; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PYRROLIDINES; STEREOISOMERISM;

EID: 77956237571     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106989h     Document Type: Article

References (52)

1. Reviews.
2. Wolfe, J. P. Synlett 2008, 2913
3. Wolfe, J. P. Eur. J. Org. Chem. 2007, 571
4. Minatti, A. and Muñiz, K. Chem. Soc. Rev. 2007, 36, 1142
5. Ney, J. E. and Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605
6. Bertrand, M. B. and Wolfe, J. P. Tetrahedron 2005, 61, 6447
7. Ney, J. E. and Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 8644
8. Bertrand, M. B. and Wolfe, J. P. Org. Lett. 2006, 8, 2353
9. Bertrand, M. B., Neukom, J. D., and Wolfe, J. P. J. Org. Chem. 2008, 73, 8851
10. Hayashi, S., Yorimitsu, H., and Oshima, K. Angew. Chem., Int. Ed. 2009, 48, 7224
11. Bagnoli, L., Cacchi, S., Fabrizi, G., Goggiamani, A., Scarponi, C., and Tiecco, M. J. Org. Chem. 2010, 75, 2134
12. Muñiz, K., Hövelmann, C. H., and Streuff, J. J. Am. Chem. Soc. 2008, 130, 763
13. Du, H., Zhao, B., and Shi, Y. J. Am. Chem. Soc. 2007, 129, 762
14. Liu, G. and Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328
15. Balazs, A., Hetenyi, A., Szakonyi, Z., Sillanpää, R., and Fülöp, F. Chem.-Eur. J. 2009, 15, 7376
16. Du, H., Yuan, W., Zhao, B., and Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688
17. Xu, L. and Shi, Y. J. Org. Chem. 2008, 73, 749
18. Cole, D. C., Lennox, W. J., Lombardi, S., Ellingboe, J. W., Bernotas, R. C., Tawa, G. J., Mazandarani, H., Smith, D. L., Zhang, G., Coupet, J., and Schechter, L. E. J. Med. Chem. 2005, 48, 353
19. Chemler has previously described enantioselective Cu-catalyzed intramolecular carboamination reactions of N -(arylsulfonyl)- N -(pent-4-enyl)amines that generate substituted tetrahydro-1 H -benzo[ e ]pyrrolo[1,2- b ][1,2]thiazinedioxides. These products can be transformed to enantiomerically enriched 2-(arylmethyl)pyrrolidines through reductive desulfonylation. See
20. Zeng, W. and Chemler, S. R. J. Am. Chem. Soc. 2007, 129, 12948
21. Zeng, W. and Chemler, S. R. J. Org. Chem. 2008, 73, 6045
22. For enantioselective intramolecular alkene carboamination reactions that proceed via Pd-catalyzed oxidative tandem cyclization of N -(2-allylphenyl) acrylamide derivatives, see
23. Yip, K.-T., Yang, M., Law, K.-L., Zhu, N.-Y., and Yang, D. J. Am. Chem. Soc. 2006, 128, 3130
24. He, W., Yip, K.-T., Zhu, N.-Y., and Yang, D. Org. Lett. 2009, 11, 5626
25. For oxidative Pd-catalyzed aminocarbonylation reactions of alkenylureas, see
26. Tsujihara, T., Shinohara, T., Takenaka, K., Takizawa, S., Onitsuka, K., Hatanaka, M., and Sasai, H. J. Org. Chem. 2009, 74, 9274
27. A complete table of results from our ligand screening experiments is provided in the Supporting Information.
28. van den Berg, M., Minnaard, A. J., Haak, R. M., Leeman, M., Schudde, E. P., Meetsma, A., Feringa, B. L., de Vries, A. H. M., Maljaars, C. E. P., Willans, C. E., Hyett, D., Boogers, J. A. F., Hubertus, H. J. W., and de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308
29. Imbos, R., Minnaard, A. J., and Feringa, B. L. Dalton. Trans. 2003, 2017-2023
30. Trost, B. M., Silverman, S. M., and Stambuli, J. P. J. Am. Chem. Soc. 2007, 129, 12398
31. Yasui, Y., Kamisaki, H., and Takemoto, Y. Org. Lett. 2008, 10, 3303
32. Reddy, V. J. and Douglas, C. J. Org. Lett. 2010, 12, 952
33. Guo, X.-X., Xie, J.-H., Hou, G.-H., Shi, W.-J., Wang, L.-X., and Zhou, Q.-L. Tetrahedron: Asymmetry 2004, 15, 2231
34. 4 led to low reactivity.
35. tBu. Aqueous workup affords the corresponding primary amines. See
36. Tom, N. J., Simon, W. M., Frost, H. N., and Ewing, M. Tetrahedron Lett. 2004, 45, 905
37. 8 was heated to 90 °C for 3 h, ca. 35% decomposition to the corresponding isocyanate was observed. This isocyanate likely is converted to the volatile pent-4-enylamine upon aqueous workup.
38. The absolute stereochemistry of 4a t was assigned based on analogy to 12.
39. Zeng, W. and Chemler, S. R. Curr. Bioact. Cmpds. 2009, 5, 2
40. Li, Z., Jin, Z., and Huang, R. Synthesis 2001, 2365
41. A recent syntheses of racemic tylophorine was reported that employed a Pd-catalyzed alkene carboamination reaction between 3a and 11 to generate the heterocyclic ring. See
42. Rossiter, L. M., Slater, M. L., Giessert, R. E., Sakwa, S. A., and Herr, R. J. J. Org. Chem. 2009, 74, 9554
43. For selected recent syntheses, see
44. Fürstner, A. and Kennedy, J. W. J. Chem.-Eur. J. 2006, 12, 7398
45. McIver, A., Young, D. D., and Dieters, A. Chem. Commun. 2008, 4750
46. Wang, Z., Li, Z., Wang, K., and Wang, Q. Eur. J. Org. Chem. 2010, 292 and references cited therein
47. 2) complexes indicate that the rates of aminopalladation and reductive elimination are comparable and that aminopalladation is not reversible under the conditions of the stoichiometric reactions. See
48. Neukom, J. D., Perch, N. S., and Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 6276
49. A related hypothesis has previously been invoked to account for the effect of reaction conditions on asymmetric induction in enantioselective intramolecular Heck reactions. See
50. Dounay, A. B. and Overman, L. E. Chem. Rev. 2003, 103, 2945 and references cited therein
51. No X-ray structural data for palladium complexes of 10 has been reported in the literature. However, this is evident in X-ray data reported for an allylpalladium complex bearing a single chiral phosphoramidite ligand derived from BINOL and bis(1-phenylethyl)amine. See
52. Mikhel, I. S., Rüegger, H., Butti, P., Camponovo, F., Huber, D., and Mezzetti, A. Organometallics 2008, 27, 2937