Enantioselective functionalization of allylic C-H bonds following a strategy of functionalization and diversification

Journal of the American Chemical Society

Volumn 135, Issue 47, 2013, Pages 17983-17989

  Sharma, Ankit ^a   Hartwig, John F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC SUBSTITUTION; BIOLOGICALLY ACTIVE MOLECULES; C-H BOND FUNCTIONALIZATION; DIASTEREO- AND ENANTIOSELECTIVITY; FUNCTIONALIZATION PROCESS; HIGH ENANTIOSELECTIVITY; OXIDATIVE FUNCTIONALIZATION; TERMINAL CARBON ATOMS;

CATALYSIS; FUNCTIONAL GROUPS; ITERATIVE METHODS; LINEAR TRANSFORMATIONS; MATHEMATICAL TRANSFORMATIONS; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

ENANTIOSELECTIVITY;

ALKENE; CARBON; HYDROGEN; IRIDIUM; NUCLEOPHILE; PALLADIUM; REAGENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVE FUNCTIONALIZATION; ENANTIOSELECTIVITY; OXIDATION; STEREOCHEMISTRY;

ALKENES; ALLYL COMPOUNDS; BENZOATES; CARBON; CATALYSIS; HYDROGEN; IRIDIUM; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM;

EID: 84889237464     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409995w     Document Type: Article

References (84)

1. Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752
2. White, M. C. Science 2012, 335, 807
3. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
4. Song, G. Y.; Wang, F.; Li, X. W. Chem. Soc. Rev. 2012, 41, 3651
5. Ramirez, T. A.; Zhao, B. G.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931
6. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
7. Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911
8. Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236
9. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851
10. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
11. Boorman, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910
12. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
13. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
14. Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242
15. Bergman, R. G. Nature 2007, 446, 391
16. Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293
17. El-Qisiari, A. K.; Qaseer, H. A.; Henry, P. M. Tetrahedron Lett. 2002, 43, 4229
18. Clark, J. S.; Roche, C. Chem. Commun. 2005, 5175
19. Zhou, Z. N.; Andrus, M. B. Tetrahedron Lett. 2012, 53, 4518
20. Hoang, V. D. M.; Reddy, P. A. N.; Kim, T. J. Organometallics 2008, 27, 1026
21. Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567
22. Malkov, A. V.; Pernazza, D.; Bell, M.; Bella, M.; Massa, A.; Teply, F.; Meghani, P.; Kocovsky, P. J. Org. Chem. 2003, 68, 4727
23. Andrus, M. B.; Zhou, Z. N. J. Am. Chem. Soc. 2002, 124, 8806
24. Chai, Z.; Rainey, T. J. J. Am. Chem. Soc. 2012, 134, 3615
25. Li, Q. A.; Yu, Z. X. Angew. Chem. 2011, 50, 2144
26. Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926
27. Covell, D. J.; White, M. C. Angew. Chem., Int. Ed. 2008, 47, 6448
28. Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2013, 52, 1739
29. Trost, B. M.; Thaisrivongs, D. A.; Donckele, J. E. Angew. Chem., Int. Ed. 2012, 52, 1523
30. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857
31. Bao, H. L.; Tambar, U. K. J. Am. Chem. Soc. 2012, 134, 18495
32. Hartwig, J. F. Organotransition metal chemistry: from bonding to catalysis; University Science Books: Sausalito, CA, 2010.
33. Tsuji, J. Palladium reagents and catalysts: new perspectives for the 21st century, 2 nd ed.; J. Wiley: Chichester, 2004.
34. Buchwald, S. L. Adv. Synth. Catal. 2004, 346, 1524
35. March, J. Advanced organic chemistry: reactions, mechanisms, and structure; McGraw-Hill: New York, 1968.
36. Leow, D.; Li, G.; Mei, T. S.; Yu, J. Q. Nature 2012, 486, 518
37. Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2012, 134, 134
38. Wang, C. M.; Chen, H.; Wang, Z. F.; Chen, J. A.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242
39. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450
40. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
41. Robbins, D. W.; Hartwig, J. F. Angew. Chem., Int. Ed. 2013, 52, 933
42. Partridge, B. M.; Hartwig, J. F. Org. Lett. 2013, 15, 140
43. Ye, Y. D.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034
44. Robbins, D. W.; Hartwig, J. F. Org. Lett. 2012, 14, 4266
45. Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864
46. Hartwig, J. F. Chem. Soc. Rev. 2011, 40, 1992
47. Liu, W. B.; Xia, J. B.; You, S. L. Top. Curr. Chem. 2012, 38, 155
48. Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147
49. Hartwig, J. F.; Pouy, M. J. Top. Organometal. Chem. 2011, 34, 169
50. Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461
51. Bartels, B.; Garcia-Yebra, C.; Rominger, F.; Helmchen, G. Eur. J. Inorg. Chem. 2002, 2569
52. Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. 1997, 36, 263
53. Polet, D.; Alexakis, A.; Tissot-Croset, K.; Corminboeuf, C.; Ditrich, K. Chem.-Eur. J. 2006, 12, 3596
54. Satyanarayana, G.; Pflasterer, D.; Helmchen, G. Eur. J. Org. Chem. 2011, 6877
55. Kim, D.; Lee, J. S.; Kong, S. B.; Han, H. Angew. Chem., Int. Ed. 2013, 52, 4203
56. Kim, D.; Reddy, S.; Singh, O. V.; Lee, J. S.; Kong, S. B.; Han, H. Org. Lett. 2013, 15, 512
57. Tsuji, J.; Sakai, K.; Nagashima, H.; Shimizu, I. Tetrahedron Lett. 1981, 22, 131
58. Hansson, S.; Heumann, A.; Rein, T.; Akermark, B. J. Org. Chem. 1990, 55, 975
59. Campbell, A. N.; White, P. B.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 15116
60. Thiery, E.; Aouf, C.; Belloy, J.; Harakat, D.; Le Bras, J.; Muzart, J. J. Org. Chem. 2010, 75, 1771
61. Liu, G. S.; Wu, Y. C. Top. Curr. Chem. 2010, 292, 195
62. Kharasch, M. S.; Sosnovsky, G. J. Am. Chem. Soc. 1958, 80, 756
63. Beckwith, A. L. J.; Zavitsas, A. A. J. Am. Chem. Soc. 1986, 108, 8230
64. Rawlinson, Dj; Sosnovsk, G. Synth.-Int. J. Methods 1972, 1
65. Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100
66. Malkov, A. V.; Baxendale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673
67. Bayardon, J.; Sinou, D.; Guala, M.; Desimoni, G. Tetrahedron: Asymmetry 2004, 15, 3195
68. Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504
69. Liu, X. Z.; Hii, K. K. J. Org. Chem. 2011, 76, 8022
70. Giri, R.; Liang, J.; Lei, J. G.; Li, J. J.; Wang, D. H.; Chen, X.; Naggar, I. C.; Guo, C. Y.; Foxman, B. M.; Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 7420
71. Tsuji, J.; Nagashima, H. Tetrahedron 1984, 40, 2699
72. Bird, C.; Booth, B. L.; Haszeldine, R. N.; Neuss, G. R. H.; Smith, M. A.; Flood, A. J. Chem. Soc., Dalton Trans. 1982, 1109
73. Yin, G. Y.; Wu, Y. C.; Liu, G. S. J. Am. Chem. Soc. 2010, 132, 11978
74. Vickers, C. J.; Mei, T. S.; Yu, J. Q. Org. Lett. 2010, 12, 2511
75. Helmchen, G. In Iridium Complexes in Organic Synthesis; Oro, L. A.; Claver, C., Eds.; Wiley-VCH: Weinheim, Germany, 2009; p 211.
76. Miyabe, H.; Takemoto, Y. Synlett 2005, 1641
77. Takeuchi, R.; Kezuka, S. Synthesis-Stuttgart 2006, 3349
78. Madrahimov, S. T.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 8136
79. Ball, M.; Gaunt, M. J.; Hook, D. F.; Jessiman, A. S.; Kawahara, S.; Orsini, P.; Scolaro, A.; Talbot, A. C.; Tanner, H. R.; Yamanoi, S.; Ley, S. V. Angew. Chem., Int. Ed. 2005, 44, 5433
80. Gaunt, M. J.; Jessiman, A. S.; Orsini, P.; Tanner, H. R.; Hook, D. F.; Ley, S. V. Org. Lett. 2003, 5, 4819
81. Gaunt, M. J.; Hook, D. F.; Tanner, H. R.; Ley, S. V. Org. Lett. 2003, 5, 4815
82. Narayan, A. R. H.; Sherman, D. H. Science 2013, 339, 283
83. Meinhold, P.; Peters, M. W.; Chen, M. M. Y.; Takahashi, K.; Arnold, F. H. ChemBioChem 2005, 6, 1765
84. Fasan, R.; Chen, M. M.; Crook, N. C.; Arnold, F. H. Angew. Chem., Int. Ed. 2007, 46, 8414