Stereoselective synthesis of densely functionalized pyrrolidin-2-ones by a conjugate addition/nitro-mannich/lactamization reaction

Journal of Organic Chemistry

Volumn 77, Issue 14, 2012, Pages 6186-6198

  Anderson, James C ^a   Horsfall, Lisa R ^a   Kalogirou, Andreas S ^a   Mills, Matthew R ^a   Stepney, Gregory J ^b   Tizzard, Graham J ^c  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; BUILDING BLOCKES; CHEMOSELECTIVE; CONJUGATE ADDITION; DIASTEREOISOMERS; DIETHYLZINC; ENANTIOPURITY; ENANTIOSELECTIVE; FUNCTIONALIZED; HIGH YIELD; IN-SITU; METHOXY; NITRO-MANNICH REACTION; ONE-POT SYNTHESIS; ORGANIC SYNTHESIS; PYRROLIDIN-2-ONES; STEREOSELECTIVE SYNTHESIS; ZINC REAGENTS;

ALDEHYDES; CATALYSIS; COPPER; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

1,3,5 TRISUBSTITUTED 4 NITROPYRROLIDIN 2 ONE DERIVATIVE; COPPER; DIETHYLZINC; NITROPYRENE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; DIASTEREOISOMER; MANNICH REACTION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

CATALYSIS; COPPER; MOLECULAR STRUCTURE; NITRO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; PYRROLIDINONES; STEREOISOMERISM; ZINC;

EID: 84864053600     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301000r     Document Type: Article

References (58)

1. Adams, H; Anderson, J. C.; Peace, S.; Pennell, A. M. K. J. Org. Chem. 1998, 63, 9932
2. Yamada, K.; Harwood, S. J.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504
3. Knudsen, K. R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K. V.; Jørgenson, K. A. J. Am. Chem. Soc. 2001, 123, 5843
4. Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625
5. Anderson, J. C.; Howell, G. P.; Lawrence, R. M.; Wilson, C. S. J. Org. Chem. 2005, 70, 5665
6. Singh, A.; Yoder, R. A.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2007, 129, 3466
7. Handa, S.; Gnanadesikan, V.; Matsungaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900
8. Gomez-Bengoa, E.; Linden, A.; López, R.; Múgica-Mendiola, I.; Oiarbe, M.; Palomo, C. J. Am. Chem. Soc. 2008, 130, 7955
9. Wang, C.-J.; Dong, X.-Q.; Zhang, Z.-H.; Xue, Z.-Y.; Teng, H.-L. J. Am. Chem. Soc. 2008, 130, 8606
10. Jakubec, P.; Helliwell, M.; Dixon, D. J. Org. Lett. 2008, 10, 4267
11. Handa, S.; Gnanadesikan, V.; Matsungaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900
12. Jiang, X.; Zhang, Y.; Wu, L.; Zhang, G.; Liu, X.; Zhang, H.; Fu, D.; Wang, R. Adv. Synth. Catal. 2009, 351, 2096
13. Handa, S.; Gnanadesikan, V.; Matsungaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 4925
14. Bernadi, L.; Bonini, B. F.; Capito, I. E.; Dessole, G.; Comes-Franchimi, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168
15. Lloyd, D. H.; Nichols, D. E. J. Org. Chem. 1986, 51, 4294
16. Barrett, A. G. M.; Spilling, C. D. Tetrahedron Lett. 1988, 29, 5733
17. Sturgess, M. A.; Yarberry, D. J. Tetrahedron Lett. 1993, 34, 4743
18. De Clercq, P. J. Chem. Rev. 1997, 97, 1755
19. Zaccardi, J.; Alluri, M.; Ashcroft, J.; Bernan, V.; Korshalla, J. D.; Morton, G. O.; Siegel, M.; Tsao, R.; Williams, D. R.; Maiese, W.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4045
20. Corey, E. J.; Gin, D. Y.; Kania, R. S J. Am. Chem. Soc. 1996, 118, 9202
21. Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625
22. Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986
23. Pan, S. C.; List, B. Org. Lett. 2007, 9, 1149
24. Anderson, J. C.; Stepney, G. J.; Mills, M. R.; Horsfall, L. R.; Blake, A. J.; Lewis, W. J. Org. Chem. 2011, 76, 1961
25. Anderson, J. C.; Blake, A. J.; Koovits, P. J.; Stepney, G. J. J. Org. Chem. 2012, 77, 4711
26. Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113
27. Guntern, A.; Ioset, J.-R.; Queiroz, E. F.; Sándor, P.; Foggin, C. M.; Hostettmann, K. J. Nat. Prod. 2003, 66, 1550
28. Li, J.; Liu, S.; Niu, S.; Zhuang, W.; Che, Y. J. Nat. Prod. 2009, 72, 2184
29. Robson, R. H.; Prescott, L. F Br. J. Clin. Pharmacol. 1979, 7, 81
30. Kazmierski, W. M.; Andrews, W. C.; Furfine, E. S.; Spaltenstein, A.; Wright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 5689
31. Sherrill, R. G.; Andrews, W. C.; Bock, W. J.; Davis-Ward, R. G.; Furfine, E. S.; Hazen, R. J.; Rutkowske, R. D.; Spaltenstein, A.; Wright, L. L. Bioorg. Med. Chem. Lett. 2005, 15, 81
32. Abou-Khalil, B. Neuropsychiatr. Dis. Treat. 2008, 4, 507
33. Enz, A.; Feuerbach, D.; Frederiksen, M. U.; Gentsch, C.; Hurth, K.; Müuller, W.; Nozulak, J.; Roy, B. L. Bioorg. Med. Chem. Lett. 2009, 19, 1287
34. Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434
35. Krawczyk, H.; Albrecht, L.; Wojciechowski, J.; Wolf, W. M.; Krajewska, U.; Rozalski, M. Tetrahedron 2008, 64, 6307
36. Dieter, R. K.; Lu, K. Tetrahedron Lett. 1999, 40, 4011
37. Basavaiah, D.; Rao, J. S. Tetrahedron Lett. 2004, 45, 1621
38. Rodriguez-Soria, V.; Quintero, L.; Sartillo-Piscil, F. Tetrahedron 2008, 64, 2750
39. Berlin, S.; Ericsson, C.; Engman, L. J. Org. Chem. 2003, 68, 8386
40. Brabandt, W.; Kimpe, N. J. Org. Chem. 2005, 70, 8717
41. Snider, B. B.; Neubert, B. J. J. Org. Chem. 2004, 69, 8952
42. Pelletier, S. M. C.; Ray, P. C.; Dixon, D. J. Org. Lett. 2011, 13, 6406
43. Pelletier, S. M. C.; Ray, P. C.; Dixon, D. J. Org. Lett. 2009, 11, 4512
44. Coles, S. J.; Gale, P. A. Chem. Sci. 2012, 3, 683-689
45. Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192
46. Scully, F. E., Jr. Heterocycles 1982, 19, 653
47. Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P. -Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229
48. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701
49. Côté, A.; Linday, V. N. G.; Charette, A. B. Org. Lett. 2007, 9, 85
50. Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829
51. Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700
52. Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369
53. Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79
54. McMurry, J. E.; Melton, J. J. Org. Chem. 1973, 38, 4367
55. Pak, C. S.; Nyerges, M. Synlett 2007, 15, 2355
56. Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; Kanter, F.; Lutz, M.; Spek, A. L.; Orru, R. Org. Lett. 2003, 5, 3759
57. Monge, D.; Jensen, K. L.; Marín, I.; Jørgensen, K. I. Org. Lett. 2011, 13, 328
58. Martin, N.; Cheng, X.; List, B. J. Am. Chem. Soc. 2008, 130, 13862