Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: Reaction development and mechanistic insights

Journal of the American Chemical Society

Volumn 132, Issue 28, 2010, Pages 9688-9692

  Parsons, Andrew T ^a   Smith, Austin G ^a   Neel, Andrew J ^a   Johnson, Jeffrey S ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; ASYMMETRIC SYNTHESIS; DONOR-ACCEPTORS; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS; ENANTIOSELECTIVE PREPARATION; IMINIUM; MECHANISTIC STUDIES; PYRROLIDINES;

ELECTRON TRANSITIONS; PROPANE;

SYNTHESIS (CHEMICAL);

ALDEHYDE; CYCLOPROPANE DERIVATIVE; IMINE; PYRROLIDINE DERIVATIVE;

ANNULATION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; ISOMERIZATION; NUCLEOPHILICITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

CYCLOPROPANES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PYRROLIDINES; STEREOISOMERISM;

EID: 77954629829     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1032277     Document Type: Article

References (61)

1. OHagan, D. Nat. Prod. Rep. 2000, 17, 435
2. For a recent review of the stereoselective preparation of substituted pyrrolidines, see: Pandey, G., Banerjee, P., and Gadre, S. R. Chem. Rev. 2006, 106, 4484
3. For selected examples, see: Pichon, M. and Figadére, B. Tetrahedron: Asymmetry 1996, 7, 927
4. Cabrera, S., Arrayas, R. G., and Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 16394
5. Bellina, F. and Rossi, R. Tetrahedron 2006, 62, 7213
6. Wolfe, J. P. Eur. J. Org. Chem. 2007, 571
7. Wang, C.-J., Liang, G., Xue, Z.-Y., and Gao, F. J. Am. Chem. Soc. 2008, 130, 17250
8. Pohlhaus, P. D. and Johnson, J. S. J. Org. Chem. 2005, 70, 1057
9. Pohlhaus, P. D. and Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014
10. Bowman, R. K. and Johnson, J. S. Org. Lett. 2006, 8, 573
11. Parsons, A. T., Campbell, M. J., and Johnson, J. S. Org. Lett. 2008, 10, 2541
12. Pohlhaus, P. D., Sanders, S. D., Parsons, A. T., Li, W., and Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642
13. Parsons, A. T. and Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 3122
14. Sanders, S. D., Ruiz-Olalla, A., and Johnson, J. S. Chem. Commun. 2009, 5135
15. Campbell, M. J. and Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 10370
16. Parsons, A. T. and Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 14202
17. Alper, P. B., Meyers, C., Lerchner, A., Siegel, D. R., and Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186
18. Sugita, Y., Kawai, K., and Yokoe, I. Heterocycles 2000, 53, 657
19. Sugita, Y., Kawai, K., and Yokoe, I. Heterocycles 2001, 55, 135
20. England, D. B., Kuss, T. D. O., Keddy, R. G., and Kerr, M. A. J. Org. Chem. 2001, 66, 4704
21. Lautens, M. and Han, W. J. Am. Chem. Soc. 2002, 124, 6312
22. Young, I. S. and Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023
23. Cardona, F. and Goti, A. Angew. Chem., Int. Ed. 2005, 44, 7832
24. Korotkov, V. S., Larionov, O. V., Hofmeister, A., Magull, J., and de Meijere, A. J. Org. Chem. 2007, 72, 7504
25. Bajtos, B., Yu, M., Zhao, H. D., and Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631
26. Perreault, C., Goudreau, S. R., Zimmer, L. E., and Charette, A. B. Org. Lett. 2008, 10, 689
27. Ivanova, O. A., Budynina, E. M., Grishin, Y. K., Trushkov, I. G., and Vereletskii, P. V. Angew. Chem., Int. Ed. 2008, 47, 1107
28. Jackson, S. K., Karadeolian, A., Driega, A. B., and Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196
29. Ivanova, O. A., Budynina, E. M., Grishin, Y. K., Trushkov, I. V., and Verteletskii, P. V. Eur. J. Org. Chem. 2008, 5329
30. Sapeta, K. and Kerr, M. A. Org. Lett. 2009, 11, 2081
31. Lebold, T. P. and Kerr, M. A. Org. Lett. 2009, 11, 4354
32. Lebold, T. P., Leduc, A. B., and Kerr, M. A. Org. Lett. 2009, 11, 3770
33. Qu, J.-P., Deng, C., Zhou, J., Sun, X.-L., and Tang, Y. J. Org. Chem. 2009, 74, 7684
34. Chagarovskiy, A. O., Budynina, E. M., Ivanova, O. A., Grishin, Y. K., Trushkov, I. V., and Verteletskii, P. V. Tetrahedron 2009, 65, 5385
35. Yadav, J. S., Reddy, B. V. S., Narasimhulu, G., Chandrakanth, D., and Satheesh, G. Synthesis 2009, 3443
36. Leduc, A. B., Lebold, T. P., and Kerr, M. A. J. Org. Chem. 2009, 74, 8414
37. Karadeolian, A. and Kerr, M. A. Angew. Chem., Int. Ed. 2010, 49, 1133
38. Wu, L. and Shi, M. Chem. - Eur. J. 2010, 16, 1149
39. Xing, S. Y., Pan, W. Y., Liu, C., Ren, J., and Wang, Z. W. Angew. Chem., Int. Ed. 2010, 49, 3215
40. Carson, C. A. and Kerr, M. A. J. Org. Chem. 2005, 70, 8242
41. Kang, Y.-B., Tang, Y., and Sun, X.-L. Org. Biomol. Chem. 2006, 4, 299
42. For enantioselective transformations of racemic D-A cyclopropanes, see: Sibi, M. P., Ma, Z., and Jasperse, C. P. J. Am. Chem. Soc. 2005, 127, 5764
43. Kang, Y.-B., Sun, X.-L., and Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 3918
44. For examples of 4-substituted pybox ligands used in asymmetric transformations, see: Nishiyama, H., Yamaguchi, S., Kondo, M., and Itoh, K. J. Org. Chem. 1992, 57, 4306
45. Park, S.-B., Murata, K., Matsumoto, H., and Nishiyama, H. Tetrahedron: Asymmetry 1995, 6, 2487
46. Clark, J. S., Clarke, M.-R., Clough, J., Blake, A. J., and Wilson, C. Tetrahedron Lett. 2004, 45, 9447
47. Wang, H., Wang, H., Liu, P., Yang, H., Xiao, J., and Li, C. J. Mol. Catal. A: Chem. 2008, 285, 128
48. Reference 4f.
49. Karimi, B. and Maleki, A. Chem. Commun. 2009, 5180 We have found that the tert -butyl substituent is optimal for chiral recognition of malonyl cyclopropanes. See: Parsons, A. T. Ph.D. Thesis, University of North Carolina, 2010.
50. 2-catalyzed annulations of aldimines and cyclopropanes, see: Reference 5a.
51. Fischer, C., Meyers, C., and Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175
52. Lerchner, A. and Carreira, E. M. J. Am. Chem. Soc. 2002, 124, 14826
53. Meyers, C. and Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 694
54. Onomura, O., Kirira, P. G., Tanaka, T., Tsukaka, S., Matsumara, Y., and Demizu, Y. Tetrahedron 2008, 64, 7498
55. For annulation results with diisopropyl 2-(4-methoxyphenyl)cyclopropane- 1,1-dicarboxylate (1d) and dibenzyl 2-(4-methoxyphenyl)cyclopropane-1,1- dicarboxylate (1e), see the Supporting Information.
56. Weitzberg, M., Abu-Shakra, E., Azeb, A., Aizenshtat, Z., and Blum, J. J. Org. Chem. 1987, 52, 529
57. Sapeta, K. and Kerr, M. A. J. Org. Chem. 2007, 72, 8597
58. Karadeolian, A. and Kerr, M. A. J. Org. Chem. 2007, 72, 10251
59. 2 for (S)- 1 should be understood to mean selective reaction of (S)- 1a, (S)- 1b, (R)- 1c, and (S)- 1d, all of which possess the same disposition of the C-2 alkyl substituent
60. CCDC 773308 and CCDC 773309 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
61. Hart, D. J. J. Am. Chem. Soc. 1980, 102, 397