Palladium/sulfoxide–phosphine-catalyzed highly enantioselective allylic etherification and amination

Chemical Communications

Volumn 50, Issue 67, 2014, Pages 9550-9553

  Feng, Bin ^a,b   Cheng, Hong Gang ^a,b   Chen, Jia Rong ^a,b   Deng, Qiao Hui ^a,b   Lu, Liang Qiu ^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

NUCLEOPHILE; PALLADIUM; PHOSPHINE; SULFOXIDE; ALKENE; ETHER DERIVATIVE; PHOSPHINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; ETHERIFICATION; SUBSTITUTION REACTION; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

ALKENES; AMINATION; ETHERS; PALLADIUM; PHOSPHINES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFOXIDES;

EID: 84904967917     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc03920c     Document Type: Article

References (45)

1. B. M. Trost and C. Lee, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley-VCH, New York, 2nd edn, 2010, pp. 593-649
2. G. Helmchen, A. Pfaltz, Acc. Chem. Res., 2000, 33, 336
3. L.-X. Dai, T. Tu, S.-L. You, W.-P. Deng, X.-L. Hou, Acc. Chem. Res., 2003, 36, 659
4. Z. Lu, S. Ma, Angew. Chem., Int. Ed., 2008, 47, 258
5. B. M. Trost, T. Zhang, J. Sieber, Chem. Sci., 2010, 1, 427
6. B. M. Trost, Org. Process Res. Dev., 2012, 16, 185
7. J. Buckingham, Dictionary of Natural Products, University Press, Cambridge, MA, 1994
8. B. M. Trost, M. L. Crawley, Chem. Rev., 2003, 103, 2921
9. A. Lumbroso, M. L. Cooke, B. Breit, Angew. Chem., Int. Ed., 2013, 52, 1890
10. B. M. Trost, F. D. Toste, J. Am. Chem. Soc., 1998, 120, 815
11. B. M. Trost, H.-C. Tsui, F. D. Toste, J. Am. Chem. Soc., 2000, 122, 3534
12. B. M. Trost, H. C. Shen, L. Dong, J. P. Surivet, J. Am. Chem. Soc., 2003, 125, 9276
13. A. R. Haight, E. J. Stoner, M. J. Peterson, V. K. Grover, J. Org. Chem., 2003, 68, 8092
14. C. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc., 2004, 126, 1628
15. C. Welter, A. Dahnz, B. Brunner, S. Streiff, P. Dübon, G. Helmchen, Org. Lett., 2005, 7, 1239
16. J.-W. Xing, P. Cao, J. Liao, Tetrahedron: Asymmetry, 2012, 23, 527
17. F. Ye, Z.-J. Zheng, L. Li, K.-F. Yang, C.-G. Xia, L.-W. Xu, Chem. Eur. J., 2013, 19, 15452
18. L. Du, P. Cao, J. Liao, Acta Chim. Sin., 2013, 71, 1239
19. C.-T. Shu, J. F. Hartwig, Angew. Chem., Int. Ed., 2004, 43, 4794
20. K. Onitsuka, H. Okuda, H. Sasai, Angew. Chem., Int. Ed., 2008, 47, 1454
21. F. L. Lam, T. T.-L. Au-Yeung, F. Y. Kwong, Z. Zhou, K. Y. Wong, A. S. C. Chan, Angew. Chem., Int. Ed., 2008, 47, 1280
22. Z.-Q. Liu, H.-F. Du, Org. Lett., 2010, 12, 3054
23. H. He, K.-Y. Ye, Q.-F. Wu, L.-X. Dai, S.-L. You, Adv. Synth. Catal., 2012, 354, 1084
24. J. Mazuela, O. Pàmies, M. Diéguez, Chem. Eur. J., 2013, 19, 2416
25. M. Coll, O. Pàmies, M. Diéguez, Org. Lett., 2014, 16, 1892
26. B.-S. Zeng, X.-Y. Yu, P. W. Siu, K. A. Scheidt, Chem. Sci., 2014, 5, 2277
27. S. F. Kirsch, L. E. Overman, J. Am. Chem. Soc., 2005, 127, 2866
28. J. S. Cannon, S. F. Kirsch, L. E. Overman, J. Am. Chem. Soc., 2010, 132, 15185
29. J.-P. Qu, L. Roßberg, G. Helmchen, J. Am. Chem. Soc., 2014, 136, 1272
30. M. Gartner, S. Mader, K. Seehafer, G. Helmchen, J. Am. Chem. Soc., 2011, 133, 2072
31. H. Miyabe, A. Matsumura, K. Moriyama, Y. Takemoto, Org. Lett., 2004, 6, 4631
32. H. Miyabe, A. Matsumura, K. Yoshida, Y. Takemoto, Tetrahedron, 2009, 65, 4464
33. Z.-P. Cao, Z.-Q. Liu, Y.-L. Liu, H.-F. Du, J. Org. Chem., 2011, 76, 6401
34. I. Lyothier, C. Defieber, E. M. Carreira, Angew. Chem., Int. Ed., 2006, 45, 6204
35. N. Kanbayashi, K. Onitsuka, Angew. Chem., Int. Ed., 2011, 50, 5197
36. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev., 2007, 107, 5133
37. T. Toru and C. Bolm, Organosulfur Chemistry in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2008
38. H. Pellissier, Chiral Sulfur Ligands: Asymmetric Catalysis, Royal Society of Chemistry, Cambridge, U.K., 2009
39. H.-G. Cheng, L.-Q. Lu, T. Wang, J.-R. Chen, W.-J. Xiao, Chem. Commun., 2012, 48, 5596
40. H.-G. Cheng, B. Feng, L.-Y. Chen, W. Guo, X.-Y. Yu, L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Chem. Commun., 2014, 50, 2873
41. K. Ouyang, Z.-F. Xi, Acta Chim. Sin., 2013, 71, 13
42. S. H. Hong, D. P. Sanders, C. W. Lee, R. H. Grubbs, J. Am. Chem. Soc., 2005, 127, 17160
43. Q. Yang, W.-J. Xiao, Z.-K. Yu, Org. Lett., 2005, 7, 871
44. M. Gatti, E. Drinkel, L.-L. Wu, I. Pusterla, F. Gaggia, R. Dorta, J. Am. Chem. Soc., 2010, 132, 15179
45. D. A. Evans, K. R. Campos, J. S. Tedrow, F. E. Michael, M. R. Gagne, J. Am. Chem. Soc., 2000, 122, 7905