Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions

Journal of the American Chemical Society

Volumn 139, Issue 6, 2017, Pages 2156-2159

  Lee, Sunggi ^a   Kaib, Philip S J ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; SILANES;

ASYMMETRIC CATALYSIS; DIHYDROBENZOFURANS; ENANTIOSELECTIVE SYNTHESIS; MECHANISTIC STUDIES; OXOCARBENIUM; OXYGEN HETEROCYCLES; TETRAHYDROFURANS;

REACTION INTERMEDIATES;

ACETIC ACID DERIVATIVE; ALIPHATIC COMPOUND; CHROMAN DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE; ION; NUCLEOPHILE; OXEPANE DERIVATIVE; OXYGEN; SILANE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; ELECTRON; ENANTIOMER; ENANTIOMERIC RATIO; ENANTIOSELECTIVITY; STEREOISOMERISM; SYNTHESIS;

EID: 85013074396     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b11993     Document Type: Article

References (77)

1. Krasnova, L.; Wong, C. H. Annu. Rev. Biochem. 2016, 85, 599 10.1146/annurev-biochem-060614-034420
2. Braun, M.; Kotter, W. Angew. Chem., Int. Ed. 2004, 43, 514 10.1002/anie.200352128
3. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198 10.1021/ja801514m
4. Benfatti, F.; Benedetto, E.; Cozzi, P. G. Chem.-Asian J. 2010, 5, 2047 10.1002/asia.201000160
5. Moquist, P. N.; Kodama, T.; Schaus, S. E. Angew. Chem., Int. Ed. 2010, 49, 7096 10.1002/anie.201003469
6. Burns, N. Z.; Witten, M. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 14578 10.1021/ja206997e
7. Maity, P.; Srinivas, H. D.; Watson, M. P. J. Am. Chem. Soc. 2011, 133, 17142 10.1021/ja207585p
8. Rueping, M.; Volla, C. M. R.; Atodiresei, I. Org. Lett. 2012, 14, 4642 10.1021/ol302084q
9. Watson, M. P.; Maity, P. Synlett 2012, 23, 1705 10.1055/s-0031-1290697
10. Cui, Y.; Villafane, L. A.; Clausen, D. J.; Floreancig, P. E. Tetrahedron 2013, 69, 7618 10.1016/j.tet.2013.05.011
11. Hsiao, C.-C.; Liao, H.-H.; Sugiono, E.; Atodiresei, I.; Rueping, M. Chem.-Eur. J. 2013, 19, 9775 10.1002/chem.201300766
12. Terada, M.; Yamanaka, T.; Toda, Y. Chem.-Eur. J. 2013, 19, 13658 10.1002/chem.201302486
13. Meng, Z.; Sun, S.; Yuan, H.; Lou, H.; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 543 10.1002/anie.201308701
14. Terada, M.; Li, F.; Toda, Y. Angew. Chem., Int. Ed. 2014, 53, 235 10.1002/anie.201307371
15. Dasgupta, S.; Rivas, T.; Watson, M. P. Angew. Chem., Int. Ed. 2015, 54, 14154 10.1002/anie.201507373
16. Srinivas, H. D.; Maity, P.; Yap, G. P. A.; Watson, M. P. J. Org. Chem. 2015, 80, 4003 10.1021/acs.joc.5b00364
17. Hardman-Baldwin, A. M.; Visco, M. D.; Wieting, J. M.; Stern, C.; Kondo, S.-i.; Mattson, A. E. Org. Lett. 2016, 18, 3766 10.1021/acs.orglett.6b01783
18. Yang, Z.; He, Y.; Toste, F. D. J. Am. Chem. Soc. 2016, 138, 9775 10.1021/jacs.6b05939
19. Ford, D. D.; Lehnherr, D.; Kennedy, C. R.; Jacobsen, E. N. ACS Catal. 2016, 6, 4616 10.1021/acscatal.6b01384
20. Ford, D. D.; Lehnherr, D.; Kennedy, C. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 138, 7860 10.1021/jacs.6b04686
21. Kennedy, C. R.; Lehnherr, D.; Rajapaksa, N. S.; Ford, D. D.; Park, Y.; Jacobsen, E. N. J. Am. Chem. Soc. 2016, 138, 13525 10.1021/jacs.6b09205
22. Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407 10.1021/cr940210s
23. Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348 10.1021/cr040629a
24. Wolfe, J. P.; Hay, M. B. Tetrahedron 2007, 63, 261 10.1016/j.tet.2006.08.105
25. Jalce, G.; Franck, X.; Figadère, B. Tetrahedron: Asymmetry 2009, 20, 2537 10.1016/j.tetasy.2009.10.034
26. Kang, S. H.; Lee, S. B.; Park, C. M. J. Am. Chem. Soc. 2003, 125, 15748 10.1021/ja0369921
27. Hennecke, U.; Müller, C. H.; Fröhlich, R. Org. Lett. 2011, 13, 860 10.1021/ol1028805
28. Denmark, S. E.; Burk, M. T. Org. Lett. 2012, 14, 256 10.1021/ol203033k
29. Miles, D. H.; Veguillas, M.; Toste, F. D. Chem. Sci. 2013, 4, 3427 10.1039/c3sc50811k
30. Zeng, X.; Miao, C.; Wang, S.; Xia, C.; Sun, W. Chem. Commun. 2013, 49, 2418 10.1039/c2cc38436a
31. Ke, Z.; Tan, C. K.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2014, 136, 5627 10.1021/ja5029155
32. Müller, C. H.; Rösner, C.; Hennecke, U. Chem.-Asian J. 2014, 9, 2162 10.1002/asia.201402229
33. Tay, D. W.; Leung, G. Y. C.; Yeung, Y.-Y. Angew. Chem., Int. Ed. 2014, 53, 5161 10.1002/anie.201310136
34. Ke, Z.; Tan, C. K.; Liu, Y.; Lee, K. G. Z.; Yeung, Y.-Y. Tetrahedron 2016, 72, 2683 10.1016/j.tet.2015.09.016
35. Blanc, A.; Toste, F. D. Angew. Chem., Int. Ed. 2006, 45, 2096 10.1002/anie.200503852
36. Jensen, K. H.; Pathak, T. P.; Zhang, Y.; Sigman, M. S. J. Am. Chem. Soc. 2009, 131, 17074 10.1021/ja909030c
37. Asano, K.; Matsubara, S. J. Am. Chem. Soc. 2011, 133, 16711 10.1021/ja207322d
38. Nising, C. F.; Bräse, S. Chem. Soc. Rev. 2012, 41, 988 10.1039/C1CS15167C
39. Cox, N.; Uehling, M. R.; Haelsig, K. T.; Lalic, G. Angew. Chem., Int. Ed. 2013, 52, 4878 10.1002/anie.201300174
40. Hintermann, L.; Ackerstaff, J.; Boeck, F. Chem.-Eur. J. 2013, 19, 2311 10.1002/chem.201203505
41. Kobayashi, Y.; Taniguchi, Y.; Hayama, N.; Inokuma, T.; Takemoto, Y. Angew. Chem. 2013, 125, 11320 10.1002/ange.201305492
42. Lu, Y.; Zou, G.; Zhao, G. ACS Catal. 2013, 3, 1356 10.1021/cs4002332
43. Azuma, T.; Murata, A.; Kobayashi, Y.; Inokuma, T.; Takemoto, Y. Org. Lett. 2014, 16, 4256 10.1021/ol501954r
44. Miyaji, R.; Asano, K.; Matsubara, S. Org. Biomol. Chem. 2014, 12, 119 10.1039/C3OB41938J
45. Ravindra, B.; Das, B. G.; Ghorai, P. Org. Lett. 2014, 16, 5580 10.1021/ol502614n
46. Ravindra, B.; Maity, S.; Das, B. G.; Ghorai, P. J. Org. Chem. 2015, 80, 7008 10.1021/acs.joc.5b00719
47. Adint, T. T.; Wong, G. W.; Landis, C. R. J. Org. Chem. 2013, 78, 4231 10.1021/jo400525w
48. Xu, K.; Zheng, X.; Wang, Z.; Zhang, X. Chem.-Eur. J. 2014, 20, 4357 10.1002/chem.201304684
49. Hosokawa, T.; Uno, T.; Inui, S.; Murahashi, S. J. Am. Chem. Soc. 1981, 103, 2318 10.1021/ja00399a030
50. Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063 10.1021/ja9701366
51. Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892 10.1002/anie.200351196
52. Zhang, Z.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2007, 46, 283 10.1002/anie.200603260
53. C-H bond activation: Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063 10.1021/ja994136c
54. Lalli, C.; van de Weghe, P. Chem. Commun. 2014, 50, 7495 10.1039/c4cc02826k
55. Liu, J.; Zhou, L.; Wang, C.; Liang, D.; Li, Z.; Zou, Y.; Wang, Q.; Goeke, A. Chem.-Eur. J. 2016, 22, 6258 10.1002/chem.201600847
56. Liu, L.; Kaib, P. S. J.; Tap, A.; List, B. J. Am. Chem. Soc. 2016, 138, 10822 10.1021/jacs.6b07240
57. Čorić, I.; List, B. Nature 2012, 483, 315 10.1038/nature10932
58. Liu, L.; Leutzsch, M.; Zheng, Y.; Alachraf, M. W.; Thiel, W.; List, B. J. Am. Chem. Soc. 2015, 137, 13268 10.1021/jacs.5b09484
59. Kaib, P. S. J.; Schreyer, L.; Lee, S.; Properzi, R.; List, B. Angew. Chem., Int. Ed. 2016, 55, 13200 10.1002/anie.201607828
60. Xie, Y.; Cheng, G. J.; Lee, S.; Kaib, P. S. J.; Thiel, W.; List, B. J. Am. Chem. Soc. 2016, 138, 14538 10.1021/jacs.6b09129
61. García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363 10.1002/anie.200901768
62. Tap, A.; Blond, A.; Wakchaure, V. N.; List, B. Angew. Chem., Int. Ed. 2016, 55, 8962 10.1002/anie.201603649
63. Zhang, Z.; Bae, H. Y.; Guin, J.; Rabalakos, C.; van Gemmeren, M.; Leutzsch, M.; Klussmann, M.; List, B. Nat. Commun. 2016, 7, 12478 10.1038/ncomms12478
64. James, T.; van Gemmeren, M.; List, B. Chem. Rev. 2015, 115, 9388 10.1021/acs.chemrev.5b00128
65. Mahlau, M.; List, B. Angew. Chem., Int. Ed. 2013, 52, 518 10.1002/anie.201205343
66. Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733 10.1021/cr020003p
67. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259 10.1016/S0040-4020(01)86671-0
68. Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 10879 10.1021/ja0524043
69. Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208 10.1021/ja993349z
70. Schmitt, A.; Reißig, H.-U. Eur. J. Org. Chem. 2000, 2000, 3893 10.1002/1099-0690(200012)2000:23<3893::AID-EJOC3893>3.0.CO;2-E
71. Shenoy, S. R.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc. 2006, 128, 8671 10.1021/ja061110u
72. Bellur, E.; Freifeld, I.; Böttcher, D.; Bornscheuer, U. T.; Langer, P. Tetrahedron 2006, 62, 7132 10.1016/j.tet.2006.03.077
73. Bloch, R.; Bortolussi, M.; Girard, C.; Seck, M. Tetrahedron 1992, 48, 453 10.1016/S0040-4020(01)89007-4
74. Cere, V.; Mazzini, C.; Paolucci, C.; Pollicino, S.; Fava, A. J. Org. Chem. 1993, 58, 4567 10.1021/jo00069a015
75. Laxmi, Y. R. S.; Iyengar, D. S. Synthesis 1996, 1996, 594 10.1055/s-1996-4256
76. Paolucci, C.; Mazzini, C.; Fava, A. J. Org. Chem. 1995, 60, 169 10.1021/jo00106a030
77. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249 10.1002/9780470147276.ch4