Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems

Journal of the American Chemical Society

Volumn 135, Issue 7, 2013, Pages 2478-2481

  Ischay, Michael A ^a   Takase, Michael K ^a   Bergman, Robert G ^b   Ellman, Jonathan A ^a  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID TREATMENTS; AZOMETHINE YLIDES; DIPOLAR CYCLOADDITIONS; ELECTROCYCLIZATION; HIGH STEREOSELECTIVITIES; PROTONATED; STEREOSELECTIVE SYNTHESIS;

CYCLOADDITION; STEREOSELECTIVITY;

STEREOCHEMISTRY;

AZABICYCLO DERIVATIVE; AZOMETHINE YLIDE; CARBON; PIPERIDINE DERIVATIVE; TROPANE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG SYNTHESIS; GEL CHROMATOGRAPHY; HYDROGEN BOND; PROTON TRANSPORT; STEREOCHEMISTRY; X RAY DIFFRACTION;

AZA COMPOUNDS; AZO COMPOUNDS; BICYCLO COMPOUNDS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; PIPERIDINES; STEREOISOMERISM; THIOSEMICARBAZONES; TROPANES;

EID: 84874083310     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja312311k     Document Type: Article

References (54)

1. Jordan, A. M; Roughly, S. D. J. Med. Chem. 2011, 54, 3451
2. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
3. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
4. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
5. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
6. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
9. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173
10. Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238
11. Hyster, T. K.; Knörr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500
12. Ye, B.; Cramer, N. Science 2012, 338, 504
13. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 6449
14. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 2350
15. Nakanish, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438
16. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013
17. Duttwyler, S.; Lu, C.; Rheingold, A. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 4064
18. Duttwyler, S.; Chen, S.; Takase, M. K.; Wiberg, K. B.; Bergman, R. G.; Ellman, J. A. Science 2013, 339, 678-682
19. Yang, D.; Micalizio, G. C. J. Am. Chem. Soc. 2012, 134, 15237
20. Wong, H.; Garnier-Amblard, E. C.; Liebeskind, L. S. J. Am. Chem. Soc. 2011, 133, 7517
21. Harrison, D. P.; Iovan, D. A.; Myers, W. H.; Sabat, M.; Wang, S.; Zottig, V. E.; Harman, W. D. J. Am. Chem. Soc. 2011, 133, 18378
22. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645
23. Martin, R. M.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2012, 77, 2501
24. For information regarding piperidine-containing drug and drug candidates, see PubChem (http://pubchem.ncbi.nlm.nih.gov/) for the structure, bioactivity, full list of published studies, and information regarding clinical trials, applications, and usage. Examples of top selling pharmaceuticals: plavix (CID 60606), oxycontin (CID 5284603), spiriva (5487426), suboxone (CID 56841117), combivent (CID 24847804), concerta (CID 9280). Select piperidine-containing drugs with multiple stereocenters: paroxetine (CID 43815), hydergine (CID 168870), moxifloxacin (CID 101526), nelfinavir (CID 64142), cabergoline (CID 83879), alvimopan (CID 5488547), morphine (CID 5464110).
25. For a review on the synthesis and elaborations of dihydropyridine derivatives, see: Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642
26. Harrison, D. P.; Sabat, M.; Myers, W. H.; Harman, W. D. J. Am. Chem. Soc. 2010, 132, 17282
27. Harschneck, T.; Kirsch, S. F. J. Org. Chem. 2011, 76, 2145
28. Tejedor, D.; Mendez-Abt, G.; García-Tellado, F. Chem.-Eur. J. 2010, 16, 428
29. Comins, D. L.; Weglarz, M. A.; O'Connor, S. Tetrahedron Lett. 1988, 29, 1751
30. Padwa, A.; Dent, W. J. Org. Chem. 1987, 52, 235
31. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484
32. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765
33. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863
34. Belanger, G.; Boudreault, J.; Levesque, F. Org. Lett. 2011, 13, 6204
35. Coldham, I.; Burrell, A. J. M.; Guerrand, H. D. S.; Oram, N. Org. Lett. 2011, 13, 1267
36. Davoren, J.; Gray, D.; Harris, A.; Nason, D.; Xu, W. Synlett 2010, 2010, 2490
37. Peese, K. M.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 1654
38. Eckelbarger, J. D.; Wilmot, J. T.; Epperson, M. T.; Thakur, C. S.; Shum, D.; Antczak, C.; Tarassishin, L.; Djaballah, H.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 4293
39. Coldham, I.; Burrell, A. J. M.; White, L. E.; Adams, H.; Oram, N. Angew. Chem., Int. Ed. 2007, 46, 6159
40. Su, S.; Porco, J. A., Jr. J. Am. Chem. Soc. 2007, 129, 7744
41. Eckelbarger, J. D.; Wilmot, J. T.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 10370
42. Pandey, G.; Laha, J. K.; Lakshmaiah, G. Tetrahedron 2002, 58, 3525
43. Pandey, G.; Sahoo, A. K.; Bagul, T. D. Org. Lett. 2000, 2, 2299
44. Pandey, G.; Laha, J. K.; Mohanakrishnan, A. K. Tetrahedron Lett. 1999, 40, 6065
45. Pandey, G.; Lakshmaiah, G.; Ghatak, A. Tetrahedron Lett. 1993, 34, 7301
46. Jones, G. S.; Savage, S. A.; Ivy, S.; Benitez, P. L.; Ramirez, A. J. Org. Chem. 2011, 76, 10332
47. Savage, S. A.; Jones, G. S.; Kolotuchin, S.; Ramrattan, S. A.; Vu, T.; Waltermire, R. E. Org. Process Res. Dev. 2009, 13, 1169
48. Augeri, D. J.; Robl, J. A.; Betebenner, D. A.; Magnin, D. R.; Khanna, A.; Robertson, J. G.; Wang, A.; Simpkins, L. M.; Taunk, P.; Huang, Q.; Han, S.-P.; Abboa-Offei, B.; Cap, M.; Xin, L.; Tao, L.; Tozzo, E.; Welzel, G. E.; Egan, D. M.; Marcinkeviciene, J.; Chang, S. Y.; Biller, S. A.; Kirby, M. S.; Parker, R. A.; Hamann, L. G. J. Med. Chem. 2005, 48, 5025
49. Vaidya, T.; Eisenberg, R.; Frontier, A. J. ChemCatChem 2011, 3, 1531
50. Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577
51. Pellissier, H. Tetrahedron 2005, 61, 6479
52. Baktharaman, S.; Afagh, N.; Vandersteen, A.; Yudin, A. K. Org. Lett. 2010, 12, 240
53. Woo, C. M.; Lu, L.; Gholap, S. L.; Smith, D. R.; Herzon, S. B. J. Am. Chem. Soc. 2010, 132, 2540
54. Williams, D. R.; Reeves, J. T. J. Am. Chem. Soc. 2004, 126, 3434