Synthesis of enantioenriched 5,6-dihydrophenanthridine derivatives through retro-carbopalladation of chiral o-bromobenzylamines

Angewandte Chemie - International Edition

Volumn 54, Issue 10, 2015, Pages 3116-3120

  Ye, Juntao ^a   LimouniDr, Aurore ^a   Zaichuk, Sonia ^a   Lautens Dr Prof, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Dihydrophenanthridines; Enantioselective synthesis; Palladium; carbon elimination

Indexed keywords

ATOMS; CATALYSIS; PALLADIUM;

ALDIMINES; CARBON ELIMINATIONS; DIHYDROPHENANTHRIDINES; ENANTIOSELECTIVE SYNTHESIS; HOMOCOUPLING REACTIONS; HYDROGEN ATOMS; ONE POT; SYNTHETIC ROUTES;

ENANTIOSELECTIVITY;

EID: 85027928252     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201411276     Document Type: Article

References (56)

1. a) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004
2. b) T. Satoh, M. Miura, Top. Organomet. Chem. 2005, 14, 1-20.
3. a) S. Chiba, Y.-J. Xu, Y.-F. Wang, J. Am. Chem. Soc. 2009, 131, 12886-12887
4. b) S.W. Youn, B. S. Kim, A. R. Jagdale, J. Am. Chem. Soc. 2012, 134, 11308-11311.
5. a) L. Mahendar, G. Satyanarayana, J. Org. Chem. 2014, 79, 2059-2074
6. b) L. Mahendar, J. Krishna, A. G. K. Reddy, B. V. Ramulu, G. Satyanarayana, Org. Lett. 2012, 14, 628-631.
7. a) M. Catellani, F. Frignani, A. Rangoni, Angew. Chem. Int. Ed. Engl. 1997, 36, 119-122
8. Angew. Chem. 1997, 109, 142-145
9. b) M. Catellani, Synlett 2003, 298-313
10. c) M. Catellani, E. Motti, N. Della Ca', Acc. Chem. Res. 2008, 41, 1512-1522
11. d) M. Malacria, G. Maestri, J. Org. Chem. 2013, 78, 1323-1328;
12. a) A. Martins, B. Mariampillai, M. Lautens, Top. Curr. Chem. 2010, 292, 1-33
13. b) H. Weinstabl, M. Suhartono, Z. Qureshi, M. Lautens, Angew. Chem. Int. Ed. 2013, 52, 5305-5308
14. Angew. Chem. 2013, 125, 5413-5416
15. c) Z. Qureshi, H. Weinstabl, M. Suhartono, H. Liu, P. Thesmar, M. Lautens, Eur. J. Org. Chem. 2014, 4053-4069.
16. a) F. R. Stermitz, K. A. Larson, D. K. Kim, J. Med. Chem. 1973, 16, 939-940
17. b) Y.-C. Chang, P.-W. Hsieh, F.-R. Chang, R.-R. Wu, C.-C. Liaw, K.-H. Lee, Y.-C. Wu, Planta Med. 2003, 69, 148-152
18. c) A. J. Molinari, M. A. Ashwell, B. H. Ridgway, A. A. Failli, W. J. Moore, PCT Int. Appl. WO 2004050631A1, 2004
19. d) S. Pegoraro, M. Lang, J. Feurle, J. Krauss, PCT Int. Appl. WO 2005105752A1, 2005
20. )B.H. Ridgway, W. J. Moore, M. A. Ashwell, W. R. Solvibile, A. T.-T. Lee, M. E. Hoke, M. Antane, A. A. Failli, PCT Int. Appl. WO 2006009831A1, 2006
21. f) J. Fotie, D. S. Bohle, M. Olivier, M. A. Gomez, S. Nzimiro, J. Nat. Prod. 2007, 70, 1650-1653
22. g) S. Pegoraro, M. Lang, T. Dreker, J. Kraus, S. Hamm, C. Meere, J. Feurle, S. Tasler, S. Prütting, Z. Kuras, V. Visan, S. Grissmer, Bioorg. Med. Chem. Lett. 2009, 19, 2299-2304
23. h) X.-J. Yang, F. Miao, Y. Yao, F.-J. Cao, R. Yang, Y.-N. Ma, B.-F. Qin, L. Zhou, Molecules 2012, 17, 13026-13035
24. i) J. Éles, G. Beke, I. Vágó, É. Bozó, J. Huszár, Á. Tarcsay, S. Kolok, É. Schmidt, M. Vastag, K. Hornok, S. Farkas, G. Domány, G. M. Keseru{combining double acute accent}, Bioorg. Med. Chem. Lett. 2012, 22, 3095-3099.
25. a) J. Finkelstein, S. Linder, J. Am. Chem. Soc. 1950, 72, 3282-3283
26. b) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211-5215
27. c) J. Barluenga, M. Fañanás-Mastral, F. Aznar, C. Valdés, Angew. Chem. Int. Ed. 2008, 47, 6594-6597
28. Angew. Chem. 2008, 120, 6696-6699
29. d) B. S. Kim, S. Y. Lee, S.W. Youn, Chem. Asian J. 2011, 6, 1952-1957
30. e) D. Intrieri, M. Mariani, A. Caselli, F. Ragaini, E. Gallo, Chem. Eur. J. 2012, 18, 10487-10490
31. f) J. K. Augustine, A. Bombrun, P. Alagarsamy, A. Jothi, Tetrahedron Lett. 2012, 53, 6280-6287.
32. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
33. 1H NMR spectra of the crude reaction mixture with the authentic samples. See the Supporting Information for details.
34. A very low yield was obtained under the optimized conditions, see the Supporting Information for details.
35. a) N. Tokunaga, Y. Otomaru, K. Okamoto, U. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13584
36. b) R. Shintani, Y. Tsutsumi, M. Nagaosa, T. Nishimura, T. Hayashi, J. Am. Chem. Soc. 2009, 131, 13588-13589
37. c) K. Okamoto, T. Hayashi, V. H. Rawal, Chem. Commun. 2009, 4815-4817
38. d) R. Shintani, M. Takeda, T. Tsuji, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 13168-13169.
39. a) R. Shintani, T. Hayashi, Aldrichimica Acta 2009, 42, 31-38
40. b) C. S. Marques, A. J. Burke, ChemCatChem 2011, 3, 635-645
41. c) P. Tian, H.-Q. Dong, G.-Q. Lin, ACS Catal. 2012, 2, 95-119.
42. a) J. Panteleev, L. Zhang, M. Lautens, Angew. Chem. Int. Ed. 2011, 50, 9089-9092
43. Angew. Chem. 2011, 123, 9255-9258
44. b) G. C. Tsui, J. Tsoung, P. Dougan, M. Lautens, Org. Lett. 2012, 14, 5542-5545
45. c) A. A. Friedman, J. Panteleev, J. Tsoung, V. Huynh, M. Lautens, Angew. Chem. Int. Ed. 2013, 52, 9755-9758
46. Angew. Chem. 2013, 125, 9937-9940
47. d) L. Zhang, L. Sonaglia, J. Stacey, M. Lautens, Org. Lett. 2013, 15, 2128-2131
48. e) J. Tsoung, J. Panteleev, M. Tesch, M. Lautens, Org. Lett. 2014, 16, 110-113
49. g) L. Zhang, Z. Qureshi, L. Sonaglia, M. Lautens, Angew. Chem. Int. Ed. 2014, 53, 13850-13853
50. Angew. Chem. 2014, 126, 14070-14073.
51. When all reagents were added at the outset of the reaction, direct Suzuki coupling reaction of the o-bromobenzaldimine 4a with phenylboroxine occurred to give the corresponding o-phenylbenzaldimine. For details on the optimization of reaction conditions, see the Supporting Information.
52. a) R. Ferraccioli, D. Carenzi, E. Motti, M. Catellani, J. Am. Chem. Soc. 2006, 128, 722-723
53. b) V. Narbonne, P. Retailleau, G. Maestri, M. Malacria, Org. Lett. 2014, 16, 628-631
54. IV complexes by X-ray crystallography, see: c) J. Vicente, A. Arcas, F. Juliá-Hernández, D. Bautista, Angew. Chem. Int. Ed. 2011, 50, 6896-6899
55. Angew. Chem. 2011, 123, 7028-7031.
56. D. J. Cárdenas, B. Martín-Matute, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 5033-5040.