Cycle-specific organocascade catalysis: Application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis

Angewandte Chemie - International Edition

Volumn 48, Issue 24, 2009, Pages 4349-4353

  Simmons, Bryon ^a   Walji, Abbas M ^a   MacMillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

Cascade reactions; Enantioselectivity; Natural products; Organocatalysis

Indexed keywords

ASYMMETRIC TRANSFORMATIONS; CASCADE REACTIONS; ENAMINES; ENANTIOSELECTIVE; HYDROAMINATIONS; IMINIUM; NATURAL PRODUCT SYNTHESIS; NATURAL PRODUCTS; ORGANOCATALYSIS;

AMINATION; AMINES; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; OLEFINS; OXIDATION; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

ALKENE; AROMADENDRANEDIOL; SESQUITERPENE;

AMINATION; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKENES; AMINATION; CATALYSIS; OXIDATION-REDUCTION; SESQUITERPENES; STEREOISOMERISM;

EID: 70349777766     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200900220     Document Type: Article

References (49)

1. a) P. A. Wender, F.C. Bi, G.G. Gamber, F. Gosselin, R. D Hubbard, M. J. C. Scanio, R. Sun, T. J. Williams, Pure Appl. Chem. 2002, 74, 25-31;
2. b) D. W C MacMillan, A.M. Walji, Synlett 2007,1477-1489.
3. "Organocascade catalysis" describes the merger of two discrete organocatalytic cycles, each of which is involved the generation of stereogenic centers. For a comprehensive description see reference [lb].
4. Organocascade catalysis: a) Y. Huang, A. M. Walji, C. H.Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051-15053. Several related manuscripts were submitted shortly after:
5. b) J. Zhou, B. List, J. Am. Chem. Soc. 2005,127, 15035-15037;
6. M. Marigo, T. Schulte, J. Fránzen, K. A. Jørgensen,7. Am. Chem. Soc. 2005,127,15710-15711.
7. a) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601;
8. Angew. Chem. Int. Ed. 2007, 46, 1570-1581;
9. b) G. Guillena, D. J. Ramon, M. Yus, Tetrahedron: Asymmetry 2007,18, 693-700;
10. H. Guo, J. Ma, Angew. Chem. 2006,118, 362-375;
11. Angew. Chem. Int. Ed. 2006, 45, 354-366.
12. Y. Chi, S. T. Scroggins, J. M. J. Fréchet, J. Am. Chem. Soc. 2008, 130, 6322-6323.
13. G. Leiais, D. W. C. MacMillan in New Frontiers in Asymmetric Catalysis (Eds. : K. Mikami, M. Lautens), Wiley, New York, 2007, pp. 313-358.
14. a) B. List, Acc. Chem. Res. 2004, 37, 548-557;
15. b) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007,107, 5471-5569.
16. For review of iminium catalysis: G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87.
17. a) I. K. Mangion, A. B. Northrup, D. W. C. MacMillan, Angew. Chem. 2004,116, 6890-6892;
18. Angew. Chem. Int. Ed. 2004, 43, 6722-6724;
19. b) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004,126, 4108-4109.
20. a) G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499;
21. b)T. E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008,108, 3795-3892.
22. T. Hayashi in Comprehensive Asymmetric Catalysis I-III, Vol. 1 (Eds.: E. N Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York 1999, pp. 351-364.
23. For an example similar to the one reported herein, see : G. Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 7417-7421.
24. a) D. A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997,119,6452-6453;
25. b) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bøgevig,K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254-6255;
26. B. List, J. Am. Chem. Soc. 2002,124, 5656-5657.
27. a) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808-10809;
28. b) G. Zhong, Angew. Chem. 2003, 115, 4379-4382;
29. Angew. Chem. Int. Ed. 2003,42,4247-4250.
30. a) A. Córdova, W. Notz, G. Zhong, J.M. Betancourt, C.F. Barbas III, J. Am. Chem. Soc. 2002,124,1842-1843;
31. b) B. List, J. Am. Chem. Soc. 2000,122, 9336-9337.
32. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797-5815.
33. a) J.F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002,124, 1172-1173;
34. b)Y.K. Chen, M. Yoshida, D.W.C. MacMillan, J Am. Chem. Soc. 2006, 128, 9328-9329;
35. S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192-1194.
36. For use of oxazoles in iminium catalysis see reference [3a]. See also S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008,130,12031-12037.
37. a) H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007,129, 11688-11689;
38. b) K. Muñiz, M. Nieger, Synlett 2003, 211-214.
39. H. Jiang, J. B. Nielsen, M. Nielsen, K. A. Jørgensen, Chem. Eur. J. 2007,13, 9068-9075.
40. D. Nilov, O. Reiser, Adv. Synth. Catal. 2002, 344, 1169-1173.
41. For amino-sulfenylation see : G.-L. Zhao, R. Rios, J. Vesely, L. Eriksson, A. Córdova, Angew. Chem. 2008, 120, 8596-8600;
42. Angew. Chem. Int. Ed. 2008, 47, 8468-8472.
43. C. M. Beechan, C. Djerassi, H. Eggert, Tetrahedron 1978, 34, 2503-2508.
44. I.C. Moriera, J. H. G. Lago, M. C. M. Young, N.F. Roque, J. Braz. Chem. Soc. 2003,14, 828-831.
45. T. Wu, Y. Chan, Y. Leu, Chem. Pharm. Bull. 2000, 3, 357-361.
46. The use of the (2R)-proline leads to diminished diastereoeselectivities as would be expected based upon catalyst control. However, we do not observe the production of enantiopure product (only 95 % ee), and as such substrate control must be influential in the final catalytic cycle.
47. CCDC 614655 contains 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.
48. J. H. Rigby, A. Bellemin, Synthesis 1988,188-189.
49. A natural product that contains one stereogenic center has been generated by the merger of two organocatalytic cycles: M. Rueping, A. P. Antonchick, T. Theissmann Angew. Chem. Int. 2006, 45, 3683-3686.