Rational design of sulfoxide-phosphine ligands for Pd-catalyzed enantioselective allylic alkylation reactions

Chemical Communications

Volumn 50, Issue 22, 2014, Pages 2873-2875

  Cheng, Hong Gang ^a,b   Feng, Bin ^a,b   Chen, Li Yan ^a,b   Guo, Wei ^a,b   Yu, Xiao Ye ^a,b   Lu, Liang Qiu ^a,b   Chen, Jia Rong ^a,b   Xiao, Wen Jing ^a,b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b Tianjin Engineering Center of Micro Nano Biomaterials and Detection Treatment Technology   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PALLADIUM; PHOSPHINE; SULFOXIDE;

ALKYLATION; ALLYLIC ALKYLATION; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY;

ALKYLATION; CATALYSIS; LIGANDS; PALLADIUM; PHOSPHINES; STEREOISOMERISM; SULFOXIDES;

EID: 84894454154     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc49488h     Document Type: Article

References (47)

1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994
2. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999
3. K. Mikami and M. Lautens, New Frontiers in Asymmetric Catalysis, Wiley, New Jersey, 2007
4. V. Caprio and J. M. J. Williams, Catalysis in Asymmetric Synthesis, Wiley, New Jersey, 2nd edn, 2009
5. I. Ojima, Catalytic Asymmetric Synthesis, Wiley, New Jersey, 3rd edn, 2010
6. T. P. Yoon, E. N. Jacobsen, Science, 2003, 299, 1691
7. Q.-L. Zhou, Privileged Chiral Ligands and Catalysts, Wiley-VCH, Weinheim, 2011
8. J.-R. Chen, H.-H. Lu, X.-Y. Li, L. Cheng, J. Wan, W.-J. Xiao, Org. Lett., 2005, 7, 4543
9. J.-R. Chen, X.-Y. Li, X.-N. Xing, W.-J. Xiao, J. Org. Chem., 2006, 71, 8198
10. J.-R. Chen, X.-L. An, X.-Y. Zhu, X.-F. Wang, W.-J. Xiao, J. Org. Chem., 2008, 73, 6006
11. H.-H. Lu, X.-F. Wang, C.-J. Yao, J.-M. Zhang, H. Wu, W.-J. Xiao, Chem. Commun., 2009, 4251
12. J.-R. Chen, Y.-J. Cao, Y.-Q. Zou, F. Tan, L. Fu, X.-Y. Zhu, W.-J. Xiao, Org. Biomol. Chem., 2010, 8, 1275
13. H.-G. Cheng, L.-Q. Lu, T. Wang, J.-R. Chen, W.-J. Xiao, Chem. Commun., 2012, 48, 5596
14. B. M. Trost, D. L. VanVranken, Chem. Rev., 1996, 96, 395
15. Z. Lu, S. Ma, Angew. Chem., Int. Ed., 2008, 47, 258
16. B. M. Trost, T. Zhang, J. Sieber, Chem. Sci., 2010, 1, 427
17. B. M. Trost, Org. Process Res. Dev., 2012, 16, 185
18. B.-L. Lei, C.-H. Ding, X.-F. Yang, X.-L. Wan, X.-L. Hou, J. Am. Chem. Soc., 2009, 131, 18250
19. J.-P. Chen, C.-H. Ding, W. Liu, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc., 2010, 132, 15493
20. J.-P. Chen, Q. Peng, B.-L. Lei, X.-L. Hou, Y.-D. Wu, J. Am. Chem. Soc., 2011, 133, 14180
21. D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. White, S. C. Virgil, B. M. Stoltz, Nat. Chem., 2012, 4, 130
22. W.-B. Liu, C. Zheng, C.-X. Zhuo, L.-X. Dai, S.-L. You, J. Am. Chem. Soc., 2012, 134, 4812
23. C.-X. Zhuo, Q.-F. Wu, Q. Zhao, Q.-L. Xu, S.-L. You, J. Am. Chem. Soc., 2013, 135, 8169
24. B. M. Trost, D. A. Thaisrivongs, E. J. Donckele, Angew. Chem., Int. Ed., 2013, 52, 1523
25. B. M. Trost, J. T. Masters, A. C. Burns, Angew. Chem., Int. Ed., 2013, 52, 2260
26. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev., 2007, 107, 5133
27. H. Pellissier, Tetrahedron, 2007, 63, 1297
28. T. Toru and C. Bolm, Organosulfur Chemistry in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2008
29. H. Pellissier, Chiral Sulfur Ligands: Asymmetric Catalysis, Royal Society of Chemistry, Cambridge, U.K., 2009
30. R. Tokunoh, M. Sodeoka, K. Aoe, M. Shibasaki, Tetrahedron Lett., 1995, 36, 8035
31. R. Siedlecka, E. Wojaczynka, J. Skarzewski, Tetrahedron: Asymmetry, 2004, 15, 1437
32. K. Hiroi, Y. Suzuki, Tetrahedron Lett., 1998, 39, 6499
33. K. Hiroi, Y. Suzuki, I. Abe, R. Kawagishi, Tetrahedron, 2000, 56, 4701
34. K. Hiroi, I. Izawa, T. Takizawa, K. Kawai, Tetrahedron, 2004, 60, 2155
35. S. Nakamura, T. Fukuzumi, T. Toru, Chirality, 2004, 16, 10
36. J. Chen, F. Lang, D. Li, L. Cun, J. Zhu, J. Deng, J. Liao, Tetrahedron: Asymmetry, 2009, 20, 1953
37. J. Xing, P. Cao, J. Liao, Tetrahedron: Asymmetry, 2012, 23, 527
38. L. Du, P. Cao, J. Xing, Y. Lou, L. Jiang, L. Li, J. Liao, Angew. Chem., Int. Ed., 2013, 52, 4207
39. J. V. Allen, J. F. Bower, J. M. J. Williams, Tetrahedron: Asymmetry, 1994, 5, 1895
40. J. F. Bower, C. J. Martin, D. J. Rawson, A. Slawin, J. Williams, J. Chem. Soc., Perkin Trans. 1, 1996, 333
41. K. Hiroi, Y. Suzuki, Heterocycles, 1997, 46, 77
42. G. Chelucci, D. Berta, A. Saba, Tetrahedron, 1997, 53, 3843
43. K. Hiroi, Y. Suzuki, I. Abe, Y. Hasegawa, K. Suzuki, Tetrahedron: Asymmetry, 1998, 9, 3797
44. J. Liu, G. Chen, J. Xing, J. Liao, Tetrahedron: Asymmetry, 2011, 22, 575
45. K. Ouyang, Z. Xi, Acta Chim. Sin., 2013, 71, 13
46. M. Pažický, V. Semak, B. Gášpár, A. Bílešová, M. Sališová, A. Bohácğ, ARKIVOC, 2008, 8, 225
47. J. Dugal-Tessier, G. R. Dake, D. P. Gates, Org. Lett., 2010, 12, 4667