Development of a novel multifunctional N,P ligand for highly enantioselective palladium-catalyzed asymmetric allylic etherification of alcohols and silanols

Chemistry - A European Journal

Volumn 19, Issue 46, 2013, Pages 15452-15457

  Ye, Fei ^a   Zheng, Zhan Jiang ^a   Li, Li ^a   Yang, Ke Fang ^a   Xia, Chun Gu ^b   Xu, Li Wen ^a,b  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

allylic etherification; asymmetric catalysis; chiral ligands; palladium; silanols

Indexed keywords

ALLYLIC ETHERIFICATION; ASYMMETRIC CATALYSIS; CHIRAL LIGAND; ENANTIOSELECTIVE; MULTIDENTATE; PALLADIUM-CATALYZED; PHOSPHORUS ATOM; SILANOLS;

ENANTIOSELECTIVITY; LIGANDS; PALLADIUM; PHOSPHORUS COMPOUNDS;

CATALYSIS;

ALCOHOL DERIVATIVE; ALLYL COMPOUND; ETHER DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; SILANE DERIVATIVE; SILANOL;

ALLYLIC ETHERIFICATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CHIRAL LIGANDS; STEREOISOMERISM;

ALLYLIC ETHERIFICATION; ASYMMETRIC CATALYSIS; CHIRAL LIGANDS; PALLADIUM; SILANOLS;

ALCOHOLS; ALLYL COMPOUNDS; CATALYSIS; ETHERS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; PHOSPHINES; SILANES; STEREOISOMERISM;

EID: 84887020931     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303233     Document Type: Article

References (84)

1. Comprehensive Asymmetric Catalysis (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, New York, 1999
2. Catalytic Asymmetric Synthesis, 3 rd ed., (Ed.: I. Ojima,), Wiley, Hoboken, NJ, 2010.
3. J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, UK, 2000
4. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, 2 nd ed., (Eds.: M. Beller, C. Bolm,), Wiley-VCH, Weinheim, 2008.
5. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069
6. Privileged Chiral Ligands and Catalysts (Ed.:, Q.L. Zhou,), Wiley-VCH, Singapore, 2011; for selected recent examples, see
7. A. Pfaltz, W. J. Drury III, Proc. Natl. Acad. Sci. USA 2004, 101, 5723-5726
8. T. Imamoto, K. Sugita, K. Yoshida, J. Am. Chem. Soc. 2005, 127, 11934
9. G. Hattori, T. Hori, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 2007, 129, 12930-12931
10. J. H. Xie, Q. L. Zhou, Acc. Chem. Res. 2008, 41, 581-593
11. S. L. Shi, L. W. Xu, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 6638-6639
12. T. Yamamoto, T. Yamada, Y. Nagata, M. Suginome, J. Am. Chem. Soc. 2010, 132, 7899-7901
13. T. Yamamoto, Y. Akai, Y. Nagata, M. Suginome, Angew. Chem. 2011, 123, 9006-9009
14. Angew. Chem. Int. Ed. 2011, 50, 8844-8847
15. T. J. Hoffman, E. M. Carreira, Angew. Chem. 2011, 123, 10858-10862
16. Angew. Chem. Int. Ed. 2011, 50, 10670-10674
17. M. Coll, K. Ahlford, O. Pàmies, H. Adlofsson, M. Diéguez, Adv. Synth. Catal. 2012, 354, 415-427
18. X. F. Jia, Z. Wang, C. G. Xia, K. L. Ding, Chem. Eur. J. 2012, 18, 15288-15295
19. T. Leõn, M. Parera, A. Roglans, A. Riera, X. Verdaguer, Angew. Chem. 2012, 124, 7057-7061
20. Angew. Chem. Int. Ed. 2012, 51, 6951-6955.
21. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943
22. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264-303
23. Angew. Chem. Int. Ed. 2008, 47, 258-297; for recent examples, see
24. K. Ohmatsu, M. Ito, T. Kunieda, T. Ooi, J. Am. Chem. Soc. 2013, 135, 590-593
25. F. Nahra, Y. Macé, D. Lambin, O. Riant, Angew. Chem. 2013, 125, 3290-3294
26. Angew. Chem. Int. Ed. 2013, 52, 3208-3212
27. B. M. Trost, J. T. Masters, A. C. Burns, Angew. Chem. 2013, 125, 2316-2320
28. Angew. Chem. Int. Ed. 2013, 52, 2260-2264
29. J. Fournier, O. Lozano, C. Menozzi, S. Arseniyadis, J. Cossy, Angew. Chem. 2013, 125, 1295-1299
30. Angew. Chem. Int. Ed. 2013, 52, 1257-1261
31. X. M. Wang, F. Y. Meng, Y. Wang, Z. B. Han, Y. J. Chen, L. Liu, Z. Wang, K. L. Ding, Angew. Chem. 2012, 124, 9410-9416
32. Angew. Chem. Int. Ed. 2012, 51, 9276-9282
33. B. M. Trost, R. Koller, B. Schäffner, Angew. Chem. 2012, 124, 8415-8418
34. Angew. Chem. Int. Ed. 2012, 51, 8290-8293
35. B. M. Trost, D. J. Michaelis, J. Charpentier, J. Xu, Angew. Chem. 2012, 124, 208-212
36. Angew. Chem. Int. Ed. 2012, 51, 204-208
37. B. M. Trost, D. A. Thaisrivongs, J. Hartwig, J. Am. Chem. Soc. 2011, 133, 12439-12441
38. B. M. Trost, K. Lehr, D. J. Michaelis, J. Xu, A. K. Buckl, J. Am. Chem. Soc. 2010, 132, 8915-8917
39. B. L. Lei, C. H. Ding, X. X. Yang, X. L. Wan, X. L. Hou, J. Am. Chem. Soc. 2009, 131, 18250-18251
40. B. M. Trost, J. Xu, T. Schmidt, J. Am. Chem. Soc. 2009, 131, 18343-18357.
41. I. GuerreroRios, A. Rosas-Hernandez, E. Martin, Molecules 2011, 16, 970-1010
42. H. Fernández-Pérez, P. Etayo, A. Panossian, A. Vidal-Ferran, Chem. Rev. 2011, 111, 2119-2176.
43. H. Kim, C. Lee, Org. Lett. 2002, 4, 4369-4371
44. D. Zhao, K. Ding, Org. Lett. 2003, 5, 1349-1351
45. A. R. Haight, E. J. Stoner, M. J. Peterson, V. K. Grover, J. Org. Chem. 2003, 68, 8092-8096
46. X. Caldentey, M. A. Pericàs, J. Org. Chem. 2010, 75, 2628-2644
47. M. Austeri, D. Linder, J. Lacour, Adv. Synth. Catal. 2010, 352, 3339-3347
48. K. N. Gavrilov, S. V. Zheglov, A. A. Shiryaev, N. N. Groshkin, E. A. Rastorguev, E. B. Benetskiy, V. A. Davankov, Tetrahedron Lett. 2011, 52, 964-968
49. M. Roggen, E. M. Carreira, Angew. Chem. 2011, 123, 5683-5686
50. Angew. Chem. Int. Ed. 2011, 50, 5568-5571
51. L. Dai, X. Li, H. Yuan, X. Li, Z. Li, D. Xu, F. Lei, Y. Liu, J. Zhang, Z. Zhou, Tetrahedron Asymm. 2011, 22, 1379-1389.
52. F. L. Lam, T. T. L. Au-Yeung, F. Y. Kwong, Z. Zhou, K. Y. Wong, A. S. C. Chan, Angew. Chem. 2008, 120, 1300-1303
53. Angew. Chem. Int. Ed. 2008, 47, 1280-1283.
54. P. Fang, C. H. Ding, X. L. Hou, L. X. Dai, Tetrahedron Asymm. 2010, 21, 1176-1178
55. M. Kato, T. Nakamura, K. Ogata, S.-I. Fukuzawa, Eur. J. Org. Chem. 2009, 5232-5238
56. Z. Liu, H. Du, Org. Lett. 2010, 12, 3054-3057
57. J. Mazuela, O. Pàmies, M. Diéguez, Chem. Eur. J. 2013, 19, 2416-2432.
58. F. Ye, Z. J. Zheng, W. H. Deng, L. S. Zheng, Y. Deng, C. G. Xia, L. W. Xu, Chem. Asian J. 2013, 8, 2242-2253.
59. L. W. Xu, J. Luo, Y. Lu, Chem. Commun. 2009, 1807-1821
60. J. C. Kizirian, Chem. Rev. 2008, 108, 140-205
61. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569.
62. K. Aikawa, M. Kojima, K. Mikami, Adv. Synth. Catal. 2010, 352, 3131-3135
63. D. W. Norman, C. A. Carraz, D. J. Hyett, P. G. Pringle, J. B. Sweeney, A. G. Orpen, H. P. Phetmung, R. L. Wingad, J. Am. Chem. Soc. 2008, 130, 6840-6847
64. K. Ding, Chem. Commun. 2008, 909-921
65. M. Nandi, J. Jin, T. V. RajanBabu, J. Am. Chem. Soc. 1999, 121, 9899-9900.
66. B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1994, 116, 4089-4090
67. B. M. Trost, M. R. Machacek, A. Aponick, Acc. Chem. Res. 2006, 39, 747-760, and references therein.
68. Y. Liu, K. Ding, J. Am. Chem. Soc. 2005, 127, 10488-10489
69. Y. Liu, C. A. Sandoval, Y. Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J. Am. Chem. Soc. 2006, 128, 14212-14213
70. B. Zhao, Z. Wang, K. Ding, Adv. Synth. Catal. 2006, 348, 1049-1057
71. B. Zhao, X. Peng, Z. Wang, C. Xia, K. Ding, Chem. Eur. J. 2008, 14, 7847-7857
72. J. Zhang, Y. Li, Z. Wang, K. Ding, Angew. Chem. 2011, 123, 11947-11951
73. Angew. Chem. Int. Ed. 2011, 50, 11743-11747
74. Y. Liu, Z. Wang, K. Wang, Acta Chim. Sinica 2012, 70, 1464-1470
75. Y. Liu, Z. Wang, K. Ding, Tetrahedron 2012, 68, 7581-7585
76. J. Zhang, K. Dong, Z. Wang, K. Ding, Org. Biomol. Chem. 2012, 10, 1598-1601
77. K. Dong, Z. Wang, K. Ding, J. Am. Chem. Soc. 2012, 134, 12474-12477.
78. N. Kise, H. Oike, E. Okazaki, M. Yoshimoto, T. Shono, J. Org. Chem. 1995, 60, 3980-3992
79. P. Hesemann, J. J. E. Moreau, T. Soto, Synth. Commun. 2003, 33, 183-189
80. G. J. Mercer, M. S. Sigman, Org. Lett. 2003, 5, 1591-1594.
81. 3 to cinnamaldehyde (up to 90 %ee or 91 %ee, respectively)
82. K. H. Wu, S. Zhou, C. A. Chen, M. C. Yang, R. T. Chiang, C. R. Chen, H. M. Gau, Chem. Commun. 2011, 47, 11668-11670
83. K. H. Wu, H. M. Gau, J. Am. Chem. Soc. 2006, 128, 14808-14809; enantioselective arylation of cinnamaldehyde with PhZnBu (up to 88 %ee)
84. L. Salvi, J. G. Kim, P. J. Walsh, J. Am. Chem. Soc. 2009, 131, 12483-12493.