Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions

Journal of Organic Chemistry

Volumn 80, Issue 8, 2015, Pages 4003-4016

  Srinivas, Harathi D ^a   Maity, Prantik ^a,b   Yap, Glenn P A ^a   Watson, Mary P ^a  

^a UNIVERSITY OF DELAWARE   (United States)

^b Biocon Limited   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL COMPOUNDS; COPPER; ORGANOMETALLICS;

ALKYNYLATIONS; CHIRAL BIS(OXAZOLINE) LIGANDS; COPPER CATALYST; COPPER CATALYZED; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; OXOCARBENIUM; OXYGEN HETEROCYCLES;

ENANTIOSELECTIVITY;

ACETAL DERIVATIVE; CHROMENE DERIVATIVE; CUPROUS ION; ISOCHROMAN DERIVATIVE; NUCLEOPHILE; BENZOPYRAN DERIVATIVE; CATION; COPPER; ORGANOMETALLIC COMPOUND; OXAZOLE DERIVATIVE;

ADDITION REACTION; ALKYNYLATION; ARTICLE; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; OPTICAL ROTATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

BENZOPYRANS; CATALYSIS; COPPER; MOLECULAR STRUCTURE; ONIUM COMPOUNDS; ORGANOMETALLIC COMPOUNDS; OXAZOLES; STEREOISOMERISM;

EID: 84928157336     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00364     Document Type: Article

References (87)

1. Albrecht, U.; Lalk, M.; Langer, P. Bioorg. Med. Chem. 2005, 13, 1531
2. TenBrink, R. E.; Bergh, C. L.; Duncan, J. N.; Harris, D. W.; Huff, R. M.; Lahti, R. A.; Lawson, C. F.; Lutzke, B. S.; Martin, I. J.; Rees, S. A.; Schlachter, S. K.; Sih, J. C.; Smith, M. W. J. Med. Chem. 1996, 39, 2435
3. Xu, J.; Kjer, J.; Sendker, J.; Wray, V.; Guan, H.; Edrada, R.; Muller, W. E. G.; Bayer, M.; Lin, W.; Wu, J.; Proksch, P. Bioorg. Med. Chem. 2009, 17, 7362
4. Bauer, D. J.; Selway, J. W. T.; Batchelor, J. F.; Tisdale, M.; Caldwell, I. C.; Young, D. A. B. Nature 1981, 292, 369
5. Lu, Z.-Y.; Lin, Z.-J.; Wang, W.-L.; Du, L.; Zhu, T.-J.; Fang, Y.-C.; Gu, Q.-Q.; Zhu, W.-M. J. Nat. Prod. 2008, 71, 543
6. Sawadjoon, S.; Kittakoop, P.; Kirtikara, K.; Vichai, V.; Tanticharoen, M.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 5470
7. Gauthier, S.; Caron, B.; Cloutier, J.; Dory, Y. L.; Favre, A.; Larouche, D.; Mailhot, J.; Ouellet, C.; Schwerdtfeger, A.; Leblanc, G.; Martel, C.; Simard, J.; Merand, Y.; Belanger, A.; Labrie, C.; Labrie, F. J. Med. Chem. 1997, 40, 2117
8. Correia, C. A.; Li, C.-J. Heterocycles 2010, 82, 555
9. Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242
10. Hayashi, M.; Inubushi, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1988, 61, 4037
11. Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2009, 131, 18057
12. Vieira, A. S.; Fiorante, P. F.; Hough, T. L. S.; Ferreira, F. P.; Ludtke, D. S.; Stefani, H. A. Org. Lett. 2008, 10, 5215
13. Vo, C.-V. T.; Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2011, 133, 14082
14. Chen, W.; Xie, Z.; Zheng, H.; Lou, H.; Liu, L. Org. Lett. 2014, 16, 5988
15. Yu, Y.; Yang, W.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2013, 52, 7586
16. Evans, D.; Thomson, R. J. Am. Chem. Soc. 2005, 127, 10506
17. Corić, I.; Vellalath, S.; List, B. J. Am. Chem. Soc. 2010, 132, 8536
18. Corić, I.; List, B. Nature 2012, 483, 315
19. Corić, I.; Muller, S.; List, B. J. Am. Chem. Soc. 2010, 132, 17370
20. Umebayashi, N.; Hamashima, Y.; Hashizume, D.; Sodeoka, M. Angew. Chem., Int. Ed. 2008, 47, 4196
21. Terada, M.; Tanaka, H.; Sorimachi, K. J. Am. Chem. Soc. 2009, 131, 3430
22. Kobayashi, S.; Arai, K.; Yamakawa, T.; Chen, Y.-J.; Salter, M. M.; Yamashita, Y. Adv. Synth. Catal. 2011, 353, 1927
23. Hoveyda, A.; Hird, A.; Kacprzynski, M. Chem. Commun. 2004, 1779
24. Ravindra, B.; Das, B. G.; Ghorai, P. Org. Lett. 2014, 16, 5580
25. Biddle, M.; Lin, M.; Scheidt, K. J. Am. Chem. Soc. 2007, 129, 3830
26. Chen, J.; Chen, J.; Lang, F.; Zhang, X.; Cun, L.; Zhu, J.; Deng, J.; Liao, J. J. Am. Chem. Soc. 2010, 132, 4552
27. Dittmer, C.; Raabe, G.; Hintermann, L. Eur. J. Org. Chem. 2007, 35, 5886
28. Korenaga, T.; Hayashi, K.; Akaki, Y.; Maenishi, R.; Sakai, T. Org. Lett. 2011, 13, 2022
29. Trost, B.; Toste, F. J. Am. Chem. Soc. 1998, 120, 9074
30. Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063
31. Wang, H.-F.; Cui, H.-F.; Chai, Z.; Li, P.; Zheng, C.-W.; Yang, Y.-Q.; Zhao, G. Chem.-Eur. J. 2009, 15, 13299
32. Wang, L.; Liu, X.; Dong, Z.; Fu, X.; Feng, X. Angew. Chem., Int. Ed. 2008, 47, 8670
33. Zhang, H.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2014, 136, 16485
34. Braun, M.; Kotter, W. Angew. Chem., Int. Ed. 2004, 43, 514
35. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198
36. Witten, M. R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2014, 53, 5912
37. Burns, N. Z.; Witten, M. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 14578
38. Terada, M.; Li, F.; Toda, Y. Angew. Chem., Int. Ed. 2014, 53, 235
39. Terada, M.; Yamanaka, T.; Toda, Y. Chem.-Eur. J. 2013, 19, 13658
40. Cui, Y.; Villafane, L. A.; Clausen, D. J.; Floreancig, P. E. Tetrahedron 2013, 69, 7618
41. Moquist, P. N.; Kodama, T.; Schaus, S. E. Angew. Chem., Int. Ed. 2010, 49, 7096
42. Hsiao, C.-C.; Liao, H.-H.; Sugiono, E.; Atodiresei, I.; Rueping, M. Chem.-Eur. J. 2013, 19, 9775
43. Rueping, M.; Volla, C. M. R.; Atodiresei, I. Org. Lett. 2012, 14, 4642
44. Meng, Z.; Sun, S.; Yuan, H.; Lou, H.; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 543
45. Benfatti, F.; Benedetto, E.; Cozzi, P. G. Chem.-Asian J. 2010, 5, 2047
46. Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687
47. Asano, Y.; Hara, K.; Ito, H.; Sawamura, M. Org. Lett. 2007, 9, 3901
48. Asano, Y.; Ito, H.; Hara, K.; Sawamura, M. Organometallics 2008, 27, 5984
49. Boyall, D.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2002, 4, 2605
50. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806
51. Ito, J.-I.; Asai, R.; Nishiyama, H. Org. Lett. 2010, 12, 3860
52. Koyuncu, H.; Dogan, Ö. Org. Lett. 2007, 9, 3477
53. Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760
54. Trost, B. M.; Chan, V. S.; Yamamoto, D. J. Am. Chem. Soc. 2010, 132, 5186
55. Yang, F.; Xi, P.; Yang, L.; Lan, J.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 5457
56. Chen, C.; Hong, L.; Xu, Z.-Q.; Liu, L.; Wang, R. Org. Lett. 2006, 8, 2277
57. Zhou, S.; Chen, C.-R.; Gau, H.-M. Org. Lett. 2010, 12, 48
58. Ahamed, M.; Todd, M. H. Eur. J. Org. Chem. 2010, 31, 5935
59. Aschwanden, P.; Stephenson, C. R. J.; Carreira, E. M. Org. Lett. 2012, 8, 2437
60. Black, D. A.; Beveridge, R. E.; Arndtsen, B. A. J. Org. Chem. 2008, 73, 1906
61. Muncipinto, G.; Moquist, P.; Schreiber, S.; Schaus, S. Angew. Chem., Int. Ed. 2011, 50, 8172
62. Taylor, A. M.; Schreiber, S. L. Org. Lett. 2006, 8, 143
63. For our initial work on isochroman acetals, see: Maity, P.; Srinivas, H. D.; Watson, M. P. J. Am. Chem. Soc. 2011, 133, 17142
64. Downey, C.; Mahoney, B.; Lipari, V. J. Org. Chem. 2009, 74, 2904
65. Maloney, D. J.; Deng, J.-Z.; Starck, S. R.; Gao, Z.; Hecht, S. M. J. Am. Chem. Soc. 2005, 127, 4140
66. Deng, J.-Z.; Starck, S. R.; Li, S.; Hecht, S. M. J. Nat. Prod. 2005, 68, 1625
67. Foo, L. Y.; Porter, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1535
68. Williamson, G.; Manach, C. Am. J. Clin. Nutr. 2005, 81, 243S
69. CCDC-973165 (8ea), CCDC-943166 (8eo), and CCDC-973164 ([(S,S)-BnBox]CuI) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
70. Wang, X.-S.; Zhao, H.; Li, Y.-H.; Xiong, R.-G.; You, X.-Z. Top. Catal. 2005, 35, 43
71. Badiei, Y. M.; Warren, T. H.; Chiang, K. P.; Holland, P. L. Inorg. Synth. 2010, 35, 50
72. Pérez-Galán, P.; Delpont, N.; Herrero-Gomez, E.; Maseras, F.; Echavarren, A. M. Chem.-Eur. J. 2010, 16, 5324
73. Hansch, C.; Leo, A.; Taft, R. Chem. Rev. 1991, 91, 165
74. Ritchie, C. D.; Sager, W. F. Prog. Phys. Org. Chem. 1964, 2, 323
75. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518
76. Matt, P. V.; L.-J, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neudurger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265
77. Shimada, T.; M, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584
78. Hirsch, K. A.; W, S. R.; Moore, J. S. J. Am. Chem. Soc. 1997, 119, 10401
79. Barett, A. G. M.; H, B. T.; Love, A. C.; Tedeschi, L. Org. Lett. 2004, 6, 835
80. Caneque, T.; C, A. M.; Alvarez-Builla, J.; Pérez-Moreno, J.; Clays, K.; Marcelo, G.; Mendicuti, F.; Castano, O.; Andrés, J. L.; Vaquero, J. J. Eur. J. Org. Chem. 2010, 33, 6323
81. Kempson, J.; G, J.; Das, J.; Moquin, R. V.; Spergel, S. H.; Watterson, S. H.; Langevine, C. M.; Dyckman, A. J.; Pattoli, M.; Burke, J. R.; Yang, X.; Gillooly, K. M.; McIntyre, K. W.; Chen, L.; Dodd, J. H.; Mckinnon, M.; Barrish, J. C.; Pitts, W. J. Bioorg. Med. Chem. Lett. 2009, 19, 2646
82. Schaate, A.; R, P.; Preuße, T.; Lohmeier, S. J.; Godt, A.; Behrens, P. Chem.-Eur. J. 2011, 17, 9320
83. Montalbetti, C.; S, M.; Bonnefis, F.; Genêt, J. P. Tetrahedron Lett. 1995, 36, 5891
84. Zubia, E.; L, F. R.; Guillermo, M. M.; Collado, I. G. Tetrahedron 1992, 48, 4239
85. Tang, Z.; Hu, Q. Adv. Synth. Catal. 2004, 346, 1635
86. Yamamoto, Y.; Kirai, N. Org. Lett. 2008, 10, 5513
87. Li, Y.; Q, Z.; Wang, H.; Fu, X.; Duan, C. J. Org. Chem. 2012, 77, 2053