Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals

Journal of the American Chemical Society

Volumn 136, Issue 35, 2014, Pages 12249-12252

  Meng, Shan Shui ^a   Liang, Yong ^b   Cao, Kou Sen ^a   Zou, Lufeng ^b   Lin, Xing Bang ^a   Yang, Hui ^a   Houk, K N ^b   Zheng, Wen Hua ^a  

^a NANJING UNIVERSITY   (China)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906857880     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja507332x     Document Type: Article

References (81)

1. Schneider, C. Synthesis 2006, 3919
2. Pineschi, M. Eur. J. Org. Chem. 2006, 4979
3. Díaz-de-Villegas, M. D.; Gálvaz, J. A.; Etayo, P.; Badorrey, R.; López-Ram-de-Víu, M. P. Chem. Soc. Rev. 2011, 40, 5564
4. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
5. Enríquez-García, á.; Kündig, E. P. Chem. Soc. Rev. 2012, 41, 7803
6. Díaz-de-Villegas, M. D.; Gálvaz, J. A.; Badorrey, R.; López-Ram-de-Víu, M. P. Chem.-Eur. J. 2012, 18, 13920
7. Sun, X.; Worthy, A. D.; Tan, K. L. Angew. Chem., Int. Ed. 2011, 50, 8167
8. Manville, N.; Alite, H.; Haeffner, F.; Hoveyda, A. H.; Snapper, M. L. Nat. Chem. 2013, 5, 768
9. Roux, C.; Candy, M.; Pons, J.-M.; Chuzel, O.; Bressy, C. Angew. Chem., Int. Ed. 2014, 53, 766
10. Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566
11. Lewis, C. A.; Chiu, A.; Kubryk, M.; Balsells, J.; Pollard, D.; Esser, C. K.; Murry, J.; Reamer, R. A.; Hansen, K. B.; Miller, S. J. J. Am. Chem. Soc. 2006, 128, 16454
12. Oriyama, T.; Taguchi, H.; Terakado, D.; Sano, T. Chem. Lett. 2002, 26
13. Lewis, C. A.; Sculimbrene, B. R.; Xu, Y.; Miller, S. J. Org. Lett. 2005, 7, 3021
14. Mizuta, S.; Tsuzuki, T.; Fujimoto, T.; Yamamoto, I. Org. Lett. 2005, 7, 3633
15. Honjo, T.; Nakao, M.; Sano, S.; Shiro, M.; Yamaguchi, K.; Sei, Y.; Nagao, Y. Org. Lett. 2007, 9, 509
16. Giustra, Z. X.; Tan, K. L. Chem. Commun. 2013, 49, 4370
17. Harada, T.; Sekiguchi, K.; Nakamura, T.; Suzuki, J.; Oku, A. Org. Lett. 2001, 3, 3309
18. Harada, T.; Egusa, T.; Igarashi, Y.; Kinugasa, M.; Oku, A. J. Org. Chem. 2002, 67, 7080
19. Harada, T.; Shiraishi, K. Synlett 2005, 1999
20. Trost, B. M.; Mino, T. J. Am. Chem. Soc. 2003, 125, 2410
21. Trost, B. M.; Malhotra, S.; Mino, T.; Rajapaksa, N. S. Chem.-Eur. J. 2008, 14, 7648
22. Jung, B.; Kang, S. H. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 1471
23. Jung, B.; Hong, M. S.; Kang, S. H. Angew. Chem., Int. Ed. 2007, 46, 2616
24. Hong, M. S.; Kim, T. W.; Jung, B.; Kang, S. H. Chem.-Eur. J. 2008, 14, 3290
25. Lee, J. Y.; You, Y. S.; Kang, S. H. J. Am. Chem. Soc. 2011, 133, 1772
26. You, Y. S.; Kim, T. W.; Kang, S. H. Chem. Commun. 2013, 49, 9669
27. Yang, W.; Yan, J.; Long, Y.; Zhang, S.; Liu, J.; Zeng, Y.; Cai, Q. Org. Lett. 2013, 15, 6022
28. Mensah, E.; Camasso, N.; Kaplan, W.; Nagorny, P. Angew. Chem., Int. Ed. 2013, 52, 12932
29. Chen, Z.; Sun, J. Angew. Chem., Int. Ed. 2013, 52, 13593
30. Ke, Z.; Tan, C. K.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2014, 136, 5627
31. Tay, D. W.; Leung, G. Y. C.; Yeung, Y.-Y. Angew. Chem., Int. Ed. 2014, 53, 5161
32. Binkley, R. W.; Goewey, G. S.; Johnson, J. C. J. Org. Chem. 1984, 49, 992
33. Sato, K.; Igarashi, T.; Yanagisawa, Y.; Kawauchi, N.; Hashimoto, H.; Yoshimura, J. Chem. Lett. 1988, 1699
34. Zhang, Z. Y.; Magnusson, G. J. Org. Chem. 1996, 61, 2394
35. Chen, Y.; Wang, P. G. Tetrahedron Lett. 2001, 42, 4955
36. Mycock, D. K.; Sherlock, A. E.; Glossop, R. A.; Hayes, C. J. Tetrahedron Lett. 2008, 49, 6390
37. Stévenin, A.; Boyer, F.-D.; Beau, J.-M. J. Org. Chem. 2010, 75, 1783
38. Akiyama, T. Chem. Rev. 2007, 107, 5744
39. Terada, M. Chem. Commun. 2008, 4097
40. You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190
41. Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2010, 291, 395
42. Terada, M. Synthesis 2010, 1929
43. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
44. Yu, J.; Shi, F.; Gong, L. Acc. Chem. Res. 2011, 44, 1156
45. Rueping, M.; Kuenkel, A.; Atodiresei, I. Chem. Soc. Rev. 2011, 40, 4939
46. Čorić, I.; Vellalath, S.; Müller, S.; Cheng, X.; List, B. Top. Organomet. Chem. 2013, 44, 165
47. Čorić, I.; Vellalath, S.; List, B. J. Am. Chem. Soc. 2010, 132, 8536
48. Xu, B.; Zhu, S.-F.; Xie, X.-L.; Shen, J.-J.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 11483
49. Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 6166
50. Jiang, J.; Xu, H.-D.; Xi, J.-B.; Ren, B.-Y.; Lv, F.-P.; Guo, X.; Jiang, L.-Q.; Zhang, Z.-Y.; Hu, W.-H. J. Am. Chem. Soc. 2011, 133, 8428
51. Maity, P.; Pemberton, R. P.; Tantillo, D. J.; Tambar, U. K. J. Am. Chem. Soc. 2013, 135, 16380
52. Coric, I.; List, B. Nature 2012, 483, 315
53. Sun, Z.; Winschel, G. A.; Borovika, A.; Nagorny, P. J. Am. Chem. Soc. 2012, 134, 8074
54. Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2013, 135, 3964
55. Wang, Z.; Law, W. K.; Sun, J. Org. Lett. 2013, 15, 5964
56. Wilent, J.; Petersen, K. S. J. Org. Chem. 2014, 79, 2303
57. Preparation of DMDO: Murray, R. W.; Singh, M. Org. Synth. 1997, 74, 91
58. Large-scale preparation of DMDO: Mikula, H.; Scatunek, D.; Lumpi, D.; Glöcklhofer, F.; Hametner, C.; Fröhlich, J. Org. Process Res. Dev. 2013, 17, 313
59. Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424
60. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
61. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363
62. Trost, B. M.; Jiang, C. Synthesis 2006, 369
63. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969
64. Mohr, J. T.; Stoltz, B. M. Chem.-Asian J. 2007, 2, 1476
65. Jautze, S.; Peters, R. Synthesis 2010, 365
66. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295
67. Shimizu, M. Angew. Chem., Int. Ed. 2011, 50, 5998
68. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593
69. Akai, S.; Tsujino, T.; Akiyama, E.; Tanimoto, K.; Naka, T.; Kita, Y. J. Org. Chem. 2004, 69, 2478
70. Kuriyama, M.; Tanigawa, S.; Kubo, Y.; Demizu, Y.; Onomura, O. Tetrahedron Asymm. 2010, 21, 1370
71. Narisano, E.; Riva, R. Tetrahedron Asymm. 1999, 10, 1223
72. All calculations were performed with: Frisch, M. L., Gaussian 09, Revision D.01; Gaussian Inc.: Wallingford, CT, 2013.
73. Geometry optimizations and frequency calculations were performed at the B3LYP/6-31G(d) level. Single-point energy calculations in acetone using the CPCM model were performed at the B3LYP-D3/6-311+G(d,p) level. For details, see the SI.
74. Zou, L.; Paton, R. S.; Eschenmoser, A.; Newhouse, T. R.; Baran, P. S.; Houk, K. N. J. Org. Chem. 2013, 78, 4037
75. In the absence of phosphoric acid, the residual water in the system can catalyze this [1,3]-proton shift process: Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.-Eur. J. 2008, 14, 4361
76. Xu, B.; Zhu, S.-F.; Zhang, Z.-C.; Yu, Z.-X.; Ma, Y.; Zhou, Q.-L. Chem. Sci. 2014, 5, 1442
77. Terada, M.; Komuro, T.; Toda, Y.; Korenaga, T. J. Am. Chem. Soc. 2014, 136, 7044
78. Calculations using the same model: Wang, H.; Jain, P.; Antilla, J. C.; Houk, K. N. J. Org. Chem. 2013, 78, 1208, and references therein
79. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. J. Am. Chem. Soc. 2002, 124, 10887
80. Wheeler, S. E.; McNeil, A. J.; Muller, P.; Swager, T. M.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 3304
81. Krenske, E. H.; Houk, K. N. Acc. Chem. Res. 2013, 46, 979