Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes

Journal of the American Chemical Society

Volumn 137, Issue 25, 2015, Pages 8069-8077

  Zhu, Rong ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ESTERS; HYDROCARBONS; STEREOCHEMISTRY;

CHEMICAL EQUATIONS; DIFUNCTIONALIZATION; ENANTIOSELECTIVE; ENANTIOSELECTIVE RADICALS; ENANTIOSELECTIVE SYNTHESIS; OXYFUNCTIONALIZATION; STEREOGENIC CENTERS; VERSATILE METHODS;

ENANTIOSELECTIVITY;

ALKENE; COPPER; COPPER COMPLEX; LACTONE; OXYGEN;

ARTICLE; CATALYST; DERIVATIZATION; DIACYLOXYLATION; ENANTIOSELECTIVITY; LACTONIZATION; OXYALKYLATION; OXYARYLATION; OXYAZIDATION; OXYSULFONYLATION; STOICHIOMETRY; SYNTHESIS; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; COPPER; LACTONES; OXYGEN; STEREOISOMERISM;

EID: 84934777138     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b04821     Document Type: Article

References (124)

1. Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348
2. Lorente, A.; Lamariano-Merketegi, J.; Albericio, F.; Álvarez, M. Chem. Rev. 2013, 113, 4567
3. Boivin, T. L. B. Tetrahedron 1987, 43, 3309
4. Tobert, J. A. Nat. Rev. Drug Discovery 2003, 2, 517
5. Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407
6. Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083
7. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981
8. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
9. Cardona, F.; Goti, A. Nat. Chem. 2009, 1, 269
10. Castellanos, A.; Fletcher, S. P. Chem.-Eur. J. 2011, 17, 5766
11. Snyder, S. A.; Treitler, D. S.; Brucks, A. P. Aldrichimica Acta 2011, 44, 27
12. Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed. 2012, 51, 10938
13. Tan, C. K.; Ling, Z.; Yeung, Y.-Y. Synlett 2011, 1335
14. Tan, C. K.; Yeung, Y.-Y. Chem. Commun. 2013, 49, 7985
15. Hennecke, U. Chem.-Asian J. 2012, 7, 456
16. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298
17. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
18. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474
19. Fujioka, H.; Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M. Angew. Chem., Int. Ed. 2010, 49, 9174
20. Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 6068
21. Wang, M.; Gao, L. X.; Yue, W.; Mai, W. P. Synth. Commun. 2004, 34, 1023
22. Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664
23. Paull, D. H.; Fang, C.; Donald, J. R.; Pansick, A. D.; Martin, S. F. J. Am. Chem. Soc. 2012, 134, 11128
24. Wilking, M.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Hennecke, U. J. Am. Chem. Soc. 2013, 135, 8133
25. Ikeuchi, K.; Ido, S.; Yoshimura, S.; Asakawa, T.; Inai, M.; Hamashima, Y.; Kan, T. Org. Lett. 2012, 14, 6016
26. Tungen, J. E.; Nolsøe, J. M. J.; Hansen, T. V. Org. Lett. 2012, 14, 5884
27. Parmar, D.; Maji, M. S.; Rueping, M. Chem.-Eur. J. 2011, 17, 5766
28. Kang, S. H.; Lee, S. B.; Park, C. M. J. Am. Chem. Soc. 2003, 125, 15748
29. Ishihara, K.; Sakakura, A.; Ukai, A. Nature 2007, 445, 900
30. Nicolaou, K. C.; Simmons, N. L.; Ying, Y.; Heretsch, P. M.; Chen, J. S. J. Am. Chem. Soc. 2011, 133, 8134
31. Cai, Y.; Liu, X.; Hui, Y.; Jiang, J.; Wang, W.; Chen, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2010, 49, 6160
32. Denmark, S. E.; Burk, M. T. Org. Lett. 2012, 14, 256
33. Chen, Z.-M.; Zhang, Q.-W.; Chen, Z.-H.; Li, H.; Tu, Y.-Q.; Zhang, F.-M.; Tan, J.-M. J. Am. Chem. Soc. 2011, 133, 8818
34. Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681
35. Huang, D.; Liu, X.; Li, L.; Cai, Y.; Liu, W.; Shi, Y. J. Am. Chem. Soc. 2013, 135, 8101
36. Lozano, O.; Blessley, G.; Martinez del Campo, T.; Thompson, A. L.; Giuffredi, G. T.; Bettati, M.; Walker, M.; Borman, R.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 8105
37. Chen, F.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2013, 135, 1232
38. Denmark, S. E.; Kalyani, D.; Collins, W. R. J. Am. Chem. Soc. 2010, 132, 15752
39. Niu, W.; Yeung, Y.-Y. Org. Lett. 2015, 17, 1660
40. Takenaka, K.; Mohanta, S. C.; Patil, M. L.; Rao, C. L.; Takizawa, S.; Suzuki, T.; Sasai, H. Org. Lett. 2010, 12, 3480
41. Zhu, R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 12655
42. Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462
43. Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120
44. Jensen, K. H.; Pathak, T. P.; Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2009, 131, 17074
45. Sequeira, F. C.; Chemler, S. R. Org. Lett. 2012, 14, 4482
46. Sun, X.; Li, X.; Song, S.; Zhu, Y.; Liang, Y.-F.; Jiao, N. J. Am. Chem. Soc. 2015, 137, 6059
47. Zhang, B.; Studer, A. Org. Lett. 2013, 15, 4548
48. Zhu, L.; Yu, H.; Xu, Z.; Jiang, X.; Wang, R. Org. Lett. 2014, 16, 1562
49. Yin, H.; Wang, T.; Jiao, N. Org. Lett. 2014, 16, 2302
50. Trahanovsky, W. S.; Robbins, M. D. J. Am. Chem. Soc. 1971, 93, 5256
51. Sequeira, F. C.; Turnpenny, B. W.; Chemler, S. R. Angew. Chem., Int. Ed. 2010, 49, 6365
52. Zhang, B.; Studer, A. Org. Lett. 2014, 16, 1790
53. Panchaud, P.; Renaud, P. J. Org. Chem. 2004, 69, 3205
54. Kong, W.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2014, 53, 5078
55. Waser, J.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 8294
56. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835
57. Bergmeier, S. C. Tetrahedron 2000, 56, 2561
58. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem. 1991, 56, 6809
59. Pedersen, C. M.; Marinescu, L. G.; Bols, M. Org. Biomol. Chem. 2005, 3, 816
60. Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192
61. Sharma, A.; Hartwig, J. F. Nature 2015, 517, 600
62. Vita, M. V.; Waser, J. Org. Lett. 2013, 15, 3246
63. Deng, Q.-H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356
64. The reaction of a 1,1-dialkyl substituted alkene derivative under standard conditions gave low yield of the oxyazidation product in essentially racemic form. This suggests that the catalyst is much less effective in distinguishing between two alkyl groups than an alkyl group and an aryl group in the tertiary radical intermediates.
65. 3 > H). (b) Some additional evidence including the result from radical clock experiments was also found consistent with the mechanism proposed in Scheme 2. See Supporting Information for details.
66. Lu, Q.; Zhang, J.; Wei, F.; Qi, Y.; Wang, H.; Liu, Z.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 7156
67. Kariya, A.; Yamaguchi, T.; Nobuta, T.; Tada, N.; Miura, T.; Itoh, A. RSC Adv. 2014, 4, 13191
68. Xi, C.; Lai, C.; Chen, C.; Wang, R. Synlett 2004, 1595
69. Taniguchi, T.; Idota, A.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 3151
70. Eto, H.; Kaneko, Y.; Takeda, S.; Tokizawa, M.; Sato, S.; Yoshida, K.; Namiki, S.; Ogawa, M.; Maebashi, K.; Ishida, K.; Matsumoto, M.; Asaoka, T. Chem. Pharm. Bull. 2001, 49, 173
71. Gala, D.; DiBenedetto, D. J.; Clark, J. E.; Murphy, B. L.; Schumacher, D. P.; Steinman, M. Tetrahedron Lett. 1996, 37, 611
72. Robin, S.; Huet, F.; Fauve, A.; Veschambre, H. Tetrahedron: Asymmetry 1993, 4, 239
73. Kozikowski, A. P.; Mugrage, B. B.; Li, C. S.; Felder, L. Tetrahedron Lett. 1986, 27, 4817
74. Tanikaga, R.; Hosoya, K.; Kaji, A. J. Chem. Soc., Perkin Trans. 1 1987, 1799
75. Wan, X.; Meng, Q.; Zhang, H.; Sun, Y.; Fan, W.; Zhang, Z. Org. Lett. 2007, 9, 26
76. Cho, B. T.; Kim, D. J. Tetrahedron: Asymmetry 2001, 12, 2043
77. Gotor, V.; Rebolledo, F.; Liz, R. Tetrahedron: Asymmetry 2001, 12, 513
78. Muñoz-Molina, J. M.; Belderraín, T. R.; Pérez, P. J. Inorg. Chem. 2010, 49, 642
79. Wolfe, J. P.; Rosi, M. A. J. Am. Chem. Soc. 2004, 126, 1620
80. Melhado, A. D.; Brenzovich, W. E.; Lackner, A. D.; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 8885
81. Zhang, G.; Cui, L.; Wang, Y.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 1474
82. Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505
83. Guo, W.; Cheng, H.-G.; Chen, L.-Y.; Xuan, J.; Feng, Z.-J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Adv. Synth. Catal. 2014, 356, 2787
84. Ball, L. T.; Green, M.; Lloyd-Jones, G. C.; Russell, C. A. Org. Lett. 2010, 12, 4724
85. Satterfield, A. D.; Kubota, A.; Sanford, M. S. Org. Lett. 2011, 13, 1076
86. Coy B., E. D.; Jovanovic, L.; Sefkow, M. Org. Lett. 2010, 12, 1976
87. Matsura, B. S.; Condie, A. G.; Buff, R. C.; Karahalis, G. J.; Stephenson, C. R. J. Org. Lett. 2011, 13, 6320
88. Zhu, R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2012, 51, 1926
89. Hartmann, M.; Li, Y.; Studer, A. J. Am. Chem. Soc. 2012, 134, 16516
90. Pathak, T. P.; Gligorich, K. M.; Welm, B. E.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870
91. Miller, Y.; Miao, L.; Hosseini, A. S.; Chemler, S. R. J. Am. Chem. Soc. 2012, 134, 12149
92. Bovino, M. T.; Liwosz, T. W.; Kendel, N. E.; Miller, Y.; Tyminska, N.; Zurek, E.; Chemler, S. R. Angew. Chem., Int. Ed. 2014, 53, 6383
93. Mai, D. N.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 12157
94. Heinrich, M. R. Chem.-Eur. J. 2009, 15, 820
95. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 2877
96. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 2886
97. Hilborn, J. W.; Pincock, J. A. J. Am. Chem. Soc. 1991, 113, 2683
98. Xie, J.; Xu, P.; Li, H.; Xue, Q.; Jin, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5672
99. Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1996, 118, 437
100. Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Dolbier, W. R., Jr.; Pan, H.-Q.; Muir, M. J. Am. Chem. Soc. 1994, 116, 99
101. Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557
102. Giese, B. Angew. Chem., Int. Ed. 1983, 22, 753
103. Janson, P. G.; Ilchenko, N. O.; Diez-Varga, A.; Szabó, K. J. Tetrahedron 2015, 71, 922
104. Kawamura, S.; Egami, H.; Sodeoka, M. J. Am. Chem. Soc. 2015, 137, 4865
105. Ling, L.; Liu, K.; Li, X.; Li, Y. ACS Catal. 2015, 5, 2458
106. Llewellyn, D. B.; Arndtsen, B. A. Can. J. Chem. 2003, 81, 1280
107. Portada, T.; Roje, M.; Hameršak, Z.; Žinić, M. Tetrahedron Lett. 2005, 46, 5957
108. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005
109. 6 precatalyst.
110. Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831
111. Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945
112. Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167
113. Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845
114. Tran, B. L.; Li, B.; Driess, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 2555
115. Wang, F.; Wang, D.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202
116. Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370
117. Lu, D.-F.; Zhu, C.-L.; Jia, Z.-X.; Xu, H. J. Am. Chem. Soc. 2014, 136, 13186
118. Zhao, B.; Du, H.; Shi, Y. J. Org. Chem. 2009, 74, 8392
119. Zultanski, S.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 15362
120. Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979
121. Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713
122. Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948
123. Gephart, R. T.; McMullin, C. L.; Sapiezynski, N. G.; Jang, E. S.; Aguila, M. J. B.; Cundari, T. R.; Warren, T. H. J. Am. Chem. Soc. 2012, 134, 17350
124. The involvement of a tertiary carbocation intermediate cannot be excluded, although a fully developed benzylic carbocation is unlikely based on the Hammett plot results.