Sterically Controlled Pd-Catalyzed Chemoselective Ketone Synthesis via N-C Cleavage in Twisted Amides

Organic Letters

Volumn 17, Issue 17, 2015, Pages 4364-4367

  Meng, Guangrong ^a   Szostak, Michal ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84941003135     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02209     Document Type: Article

References (57)

1. Metal-Catalyzed Cross-Coupling Reactions and More; de Meijere, A., Bräse, S., Oestreich, M., Eds.; Wiley: New York, 2014.
2. Science of Synthesis: Cross-Coupling and Heck-Type Reactions; Molander, G., Wolfe, J. P., Larhed, M., Eds.; Thieme: Stuttgart, 2013.
3. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
4. Dieter, R. K. Tetrahedron 1999, 55, 4177 10.1016/S0040-4020(99)00184-2
5. Zapf, A. Angew. Chem., Int. Ed. 2003, 42, 5394 10.1002/anie.200301681
6. Gooßen, L. J.; Rodriguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100 10.1002/anie.200704782
7. Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis; Pergamon Press: 1991.
8. Smith, M. B.; March, J. Advanced Organic Chemistry; Wiley: Hoboken, NJ, 2007.
9. Negishi, E.; Bagheri, V.; Chatterjee, S.; Luo, F. T.; Miller, J. A.; Stoll, A. T. Tetrahedron Lett. 1983, 24, 5181 10.1016/S0040-4039(00)88391-4
10. Milstein, D.; Stille, J. K. J. Org. Chem. 1979, 44, 1613 10.1021/jo01324a006
11. Fukuyama, T.; Tokuyama, H. Aldrichimica Acta 2004, 37, 87
12. Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260 10.1021/ja005613q
13. Prokopcova, H.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 2276 10.1002/anie.200802842
14. Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137 10.1246/bcsj.75.137
15. Gooßen, L. J.; Ghosh, K. Angew. Chem., Int. Ed. 2001, 40, 3458 10.1002/1521-3773(20010917)40:18<3458::AID-ANIE3458>3.0.CO;2-0
16. Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615 10.1021/jo0492719
17. Tatamidani, H.; Kakiuchi, F.; Chatani, N. Org. Lett. 2004, 6, 3597 10.1021/ol048513o
18. Xin, B.; Zhang, Y.; Cheng, K. J. Org. Chem. 2006, 71, 5725 10.1021/jo060749d
19. Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114 10.1002/anie.200900013
20. Hermange, P.; Lindhardt, A. T.; Taaning, R. H.; Bjerglund, K.; Lupp, D.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 6061 10.1021/ja200818w
21. Greenberg, A.; Breneman, C. M.; Liebman, J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science; Wiley-VCH: 2003.
22. Laurence, C.; Gal, J. F. Lewis Basicity and Affinity Scales: Data and Measurement; Wiley-Blackwell: 2009.
23. New Trends in Cross-Coupling; Colacot, T. J., Ed.; The Royal Society of Chemistry: Cambridge, 2015.
24. Winkler, F. K.; Dunitz, J. D. J. Mol. Biol. 1971, 59, 169 10.1016/0022-2836(71)90419-0
25. Szostak, M.; Aubé, J. Chem. Rev. 2013, 113, 5701 10.1021/cr4000144
26. Pracejus, H. Chem. Ber. 1959, 92, 988 10.1002/cber.19590920435
27. Kirby, A. J.; Komarov, I. V.; Wothers, P. D.; Feeder, N. Angew. Chem., Int. Ed. 1998, 37, 785 10.1002/(SICI)1521-3773(19980403)37:6<785::AID-ANIE785>3.0.CO;2-J
28. Tani, K.; Stoltz, B. M. Nature 2006, 441, 731 10.1038/nature04842
29. Lei, Y.; Wrobleski, A. D.; Golden, J. E.; Powell, D. R.; Aubé, J. J. Am. Chem. Soc. 2005, 127, 4552 10.1021/ja050214m
30. Greenberg, A.; Venanzi, C. A. J. Am. Chem. Soc. 1993, 115, 6951 10.1021/ja00068a064
31. Greenberg, A.; Moore, D. T.; DuBois, T. D. J. Am. Chem. Soc. 1996, 118, 8658 10.1021/ja960294h
32. Bennet, A. J.; Wang, Q. P.; Slebocka-Tilk, H.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1990, 112, 6383 10.1021/ja00173a029
33. Bennet, A. J.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563 10.1021/ja00020a017
34. Cox, C.; Lectka, T. Acc. Chem. Res. 2000, 33, 849 10.1021/ar990165g
35. Szostak, R.; Aubé, J.; Szostak, M. Chem. Commun. 2015, 51, 6395 10.1039/C5CC01034A
36. Szostak, R.; Aubé, J.; Szostak, M. J. Org. Chem. 2015, 80, 7905 10.1021/acs.joc.5b00881
37. Yamada, S. Rev. Heteroatom. Chem. 1999, 19, 203
38. Hutchby, M.; Houlden, C. E.; Haddow, M. F.; Tyler, S. N.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. Angew. Chem., Int. Ed. 2012, 51, 548 10.1002/anie.201107117
39. Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046 10.1021/ja034908b
40. Xie, L. G.; Wang, Z. X. Angew. Chem., Int. Ed. 2011, 50, 4901 10.1002/anie.201100683
41. Tobisu, M.; Nakamura, K.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 5587 10.1021/ja501649a
42. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
43. Li, X.; Zou, G. Chem. Commun. 2015, 51, 5089 10.1039/C5CC00430F
44. Hie, L.; Nathel, N. F. F.; Shah, T. K.; Baker, E. L.; Hong, X.; Yang, Y. F.; Liu, P.; Houk, K. N.; Garg, N. K. Nature 2015, 524, 79 10.1038/nature14615
45. Lennox, A. J. J.; Lloyd-Jones, G. C. Chem. Soc. Rev. 2014, 43, 412 10.1039/C3CS60197H
46. Sato, T.; Chida, N. Org. Biomol. Chem. 2014, 12, 3147 10.1039/c4ob00389f
47. Otani, Y.; Nagae, O.; Naruse, Y.; Inagaki, S.; Ohno, M.; Yamaguchi, K.; Yamamoto, G.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2003, 125, 15191 10.1021/ja036644z
48. Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073 10.1021/ja1073799
49. Gooßen, L. J.; Rodriguez, N. Chem. Commun. 2004, 724.
50. Liu, Y.; Kim, K. E.; Herbert, M. B.; Fedorov, A.; Grubbs, R. H.; Stoltz, B. M. Adv. Synth. Catal. 2014, 356, 130 10.1002/adsc.201301109
51. John, A.; Hogan, L. T.; Hillmyer, M. A.; Tolman, W. B. Chem. Commun. 2015, 51, 2731 10.1039/C4CC09003A
52. Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, 1994, 149 10.1055/s-1994-22773
53. Santos, L. S. Eur. J. Org. Chem. 2008, 2008, 235 10.1002/ejoc.200700723
54. Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926 10.1021/ja710731a
55. Gooßen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. J. Am. Chem. Soc. 2005, 127, 11102 10.1021/ja052435y
56. Lennox, A. J. J.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2013, 52, 7362 10.1002/anie.201301737
57. Partyka, D. V. Chem. Rev. 2011, 111, 1529 10.1021/cr1002276