Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: Controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams

Journal of the American Chemical Society

Volumn 135, Issue 23, 2013, Pages 8504-8507

  White, Nicholas A ^a   Dirocco, Daniel A ^a   Rovis, Tomislav ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL N-HETEROCYCLIC CARBENES; DIASTEREOMERS; HIGH STEREOSELECTIVITIES; INTERMOLECULAR REACTIONS; N-HETEROCYCLIC CARBENES; NITROALKENES; NITROESTERS; ONE-POT PROCEDURES;

AMIDES; CATALYSIS; STEREOCHEMISTRY; STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

2 PIPERIDONE DERIVATIVE; CARBENE; CINNAMALDEHYDE; HETEROCYCLIC COMPOUND; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DECOMPOSITION; DIASTEREOISOMER; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; PROTON TRANSPORT; REACTION OPTIMIZATION; STEREOCHEMISTRY;

ALKENES; CATALYSIS; HETEROCYCLIC COMPOUNDS; LACTAMS; METHANE; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 84878933614     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja403847e     Document Type: Article

References (43)

1. Moore, J. L.; Rovis, T. Top. Curr. Chem. 2010, 291, 77
2. Vora, H. U.; Rovis, T. Aldrichimica Acta 2011, 44, 1
3. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511-3522
4. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691-2698
5. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336-5346
6. Chiang, P.-C.; Bode, J. W. TCI MAIL. 2011, 149, 2-17
7. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53-57
8. Vora, H. U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617-1639
9. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371
10. Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205-6208
11. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131-3134
12. Rommel, M.; Fukuzumi, T.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 17266-17267
13. Raup, D. E. A.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766-771
14. Zhao, X.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466-12469
15. Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736-8737
16. Chiang, P.-C.; Kaeobamrung, J.; Bode, J. W. J. Am. Chem. Soc. 2007, 129, 3520-3521
17. Cardinal-David, B.; Raup, D. E. A.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345-5347
18. Nair, V.; Poonoth, M.; Vellalath, S.; Suresh, E.; Thirumalai, R. J. Org. Chem. 2006, 71, 8964-8965
19. Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2416-2417
20. Kathiravan, M. K.; Salake, A. B.; Chothe, A. S.; Dudhe, P. B.; Watode, R. P.; Mukta, M. S.; Gadhwe, S. Bioorg. Med. Chem. 2012, 20, 5678-5698
21. Khadem, S.; Marles, R. J. Molecules 2012, 17, 191-206
22. Modern Alkaloids: Structure, Isolation, Synthesis and Biology; Fattorusso, E.; Taglialatela- Scafati, O., Eds; Wiley-VCH: Weinheim, Germany, 2008.
23. Strunz, G. M.; Findlay, J. A. in The Alkaloids, Vol. 26 (Ed.: Brossi, A.), Academic Press, New York, 1985, pp 89.
24. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435
25. Michael, J. P. Nat. Prod. Rep. 2008, 25, 166-187
26. Nair, V.; Sinu, C. R.; Babu, B. P.; Varghese, V.; Jose, A.; Suresh, E. Org. Lett. 2009, 11, 5570-5573
27. Maji, B.; Ji, L.; Wang, S.; Vedachalam, S.; Rakesh, G.; Liu, X.-W. Angew. Chem., Int. Ed. 2012, 51, 8276-8280
28. DiRocco, D. A.; Oberg, K, M.; Dalton, D. M.; Rovis, T. J. Am. Chem. Soc. 2009, 131, 10872-10874
29. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 10402-10405
30. DiRocco, D. A.; Noey, E. L.; Houk, K. N.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 2391-2394
31. During review of this manuscript, Ye published an aza-benzoin between enals and ketimines; see Sun, L.-H.; Liang, Z.-Q.; Jia, W.-Q.; Ye, S. Angew. Chem., Int. Ed. 2013, 10.1002/anie.201301304
32. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299
33. Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876-8877
34. Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134-3138
35. Enders, D.; Han, J. Tetrahedron Asymmetry 2008, 19, 1367-1371
36. He, L.; Lv, H.; Zhang, Y.-R.; Ye, S. J. Org. Chem. 2008, 73, 8101-8103
37. Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905-908
38. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873-3876
39. Bode has reported two complementary approaches for the direct asymmetric synthesis of δ-lactams (dihydropyridinones, specifically) via NHC catalysis; from enals and unsaturated imines: He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418-8420
40. from enals and stable enamines: Wanner, B.; Mahatthananchai, J.; Bode, J. W. Org. Lett. 2011, 13, 5378-5381
41. Senkus, M. Ind. Eng. Chem. 1948, 40, 506
42. Regan, B. M.; Hayes, F. N. F. J. Am. Chem. Soc. 1956, 78, 639-643
43. Hacksell, U.; Arvidsson, L. E.; Svensson, U.; Nilsson, J. L. G.; Sanchez, D.; Wikstroem, H.; Lindberg, P.; Hjorth, S.; Carlsson, A. J. Med. Chem. 1981, 24, 1475-1482