An Unexpected inversion of enantioselectivity in a copper-catalyzed intramolecular desymmetric aryl C-N coupling reaction

Synthesis (Germany)

Volumn 46, Issue 14, 2014, Pages 1917-1923

  Liu, Jiangguang ^a   Yan, Jiajie ^a   Qin, Dongguang ^a,b   Cai, Qian ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b ABA Chemicals Corporation   (China)

Author keywords

asymmetric desymmetrization; copper catalysis; indolines; inversion; N arylation

Indexed keywords

AMINO ACIDS; CATALYSIS; COPPER;

COPPER CATALYSIS; DESYM-METRIZATION; INDOLINES; INVERSION; N-ARYLATIONS;

ENANTIOSELECTIVITY;

4 (N,N DIMETHYLAMINO)PYRIDINE; ALPHA,ALPHA BIS(2 IODOBENZYL)GLYCINE; CARBOXYLIC ACID DERIVATIVE; COPPER; DIMETHYL SULFOXIDE; GLYCINE; INDOLE DERIVATIVE; INDOLINE DERIVATIVE; N,N DIMETHYLFORMAMIDE; OCTAHYDRO 1H INDOLE 2 CARBOXYLIC ACID; POTASSIUM DIHYDROGEN PHOSPHATE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; ASYMMETRIC DESYMMETRIZATION; CATALYSIS; CHEMICAL REACTION; COUPLING REACTION; ENANTIOSELECTIVITY;

EID: 84904047535     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338638     Document Type: Article

References (44)

1. Current address: Department of Chemistry, Uppsala University, Box 576, SE-751 23 Uppsala, Sweden.
2. Corey E. J., Kurti L. Enantioselective Chemical Synthesis: Methods, Logic and Practice. Direct Book Publishing Dallas, Texas: 2011
3. Gawley R. E., Aubé J. Principles of Asymmetric Synthesis. 2nd ed Elsevier Kidlington, Oxford, UK: 2012
4. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed; de Meijere A., Diederich F. Wiley-VCH Weinheim: 2004
5. Applied Cross-Coupling Reactions. Nishihara Y. Springer Berlin, Heidelberg: 2013
6. Ley S. V., Thomas A. W. Angew. Chem. Int. Ed.: 2003; 42 5400
7. Beletskaya I. P., Cheprakov A. V. Coord. Chem. Rev.: 2004; 248 2337
8. Evano G., Blanchard N., Toumi M. Chem. Rev.: 2008; 108 3054
9. Monnier F., Taillefer M. Angew. Chem. Int. Ed.: 2009; 48 6954
10. Ma D., Cai Q. Acc. Chem. Res.: 2008; 41 1450
11. Surry D. S., Buchwald S. L. Chem. Sci.: 2010; 1 13
12. Kitagawa O., Takahashi M., Yoshikawa M., Taguchi T. J. Am. Chem. Soc.: 2005; 127 3676
13. Kitagawa O., Yoshikawa M., Tanabe H., Morita T., Takahashi M., Dobashi Y., Taguchi T. J. Am. Chem. Soc.: 2006; 128 12923
14. Kitagawa O., Kurihara D., Tanabe H., Shibuya T., Taguchi T. Tetrahedron Lett.: 2008; 49 471
15. Takenaka K., Itoh N., Sasai H. Org. Lett.: 2009; 11 1483
16. Porosa L., Viirre R. D. Tetrahedron Lett.: 2009; 50 4170
17. Rossen K., Pye P. J., Maliakal A., Volante R. P. J. Org. Chem.: 1997; 62 6462
18. Tagashira J., Imao D., Yamamoto T., Ohta T., Furukawa I., Ito Y. Tetrahedron: Asymmetry: 2005; 16 2307
19. Kreis M., Friedmann C. J., Bräse S. Chem. Eur. J.: 2005; 11 7387
20. Salih M. Q., Beaudry C. M. Org. Lett.: 2013; 15 4540
21. Zhou F., Guo J., Liu J., Ding K., Yu S., Cai Q. J. Am. Chem. Soc.: 2012; 134 14326
22. Cai Q., Zhou F. Synlett: 2013; 24 408
23. Yang W., Long Y., Zhang S., Zeng Y., Cai Q. Org. Lett.: 2013; 15 3598
24. Yang W., Yan J., Long Y., Zhang S., Liu J., Zeng Y., Cai Q. Org. Lett.: 2013; 15 6022
25. García-Urdiales E., Alfonso I., Gotor V. Chem. Rev.: 2005; 105 313
26. Willis M. C. J. Chem. Soc., Perkin Trans. 1: 1999; 1765
27. Studer A., Schleth F. Synlett: 2005; 3033
28. Rovis T. In New Frontiers in Asymmetric Catalysis. Mikami K., Lautens M. John Wiley & Sons Hoboken, NJ: 2007; 275 309
29. Takano S., Iwabuchi Y., Ogasawara K. J. Am. Chem. Soc.: 1991; 113 2786
30. Tawaki S., Klibanov A. J. Am. Chem. Soc.: 1992; 114 1882
31. Ferey V., Vedrenne P., Toupet L., Gall T. L., Mioskowski C. J. Org. Chem.: 1996; 61 7244
32. von Arx M., Mallat T., Baiker A. Angew. Chem. Int. Ed.: 2001; 40 2302
33. Bonalumi N., Vargas A., Ferri D., Bürgi T., Mallat T., Baiker A. J. Am. Chem. Soc.: 2005; 127 8467
34. Bartsch S., Kourist R., Bornscheuer U. T. Angew. Chem. Int. Ed.: 2008; 47 1508
35. Sarotti A. M., Fernández I., Spanevello R. A., Sierra M. Á, Suárez A. G. Org. Lett.: 2008; 10 3389
36. Szollosi G., Busygin I., Herman B., Leino R., Bucsi I., Murzin D. Y., Fülöp F., Bartók M. ACS Catal.: 2011; 1 1316
37. McInturff E. L., Yamaguchi E., Krische M. J. J. Am. Chem. Soc.: 2012; 134 20628
38. Pratter S. M., Konstantinovics C., Di Giuro C. M. L, Leitner E., Kumar D., de Visser S. P., Grogan G., Straganz G. D. Angew. Chem. Int. Ed.: 2013; 52 9677
39. Huang Z., Hartwig J. F. Angew. Chem. Int. Ed.: 2012; 51 1028
40. Chen B., Hou X.-L, Li Y.-X, Wu Y.-D. J. Am. Chem. Soc.: 2011; 133 7668
41. Huffmann L. M., Stahl S. S. Dalton Trans.: 2011; 40 8959
42. Casitas A., King A. E., Parella T., Costas M., Stahl S. S., Ribas X. Chem. Sci.: 2010; 1 326
43. Strieter E. R., Bhayana B., Buchwald S. L. J. Am. Chem. Soc.: 2009; 131 78
44. Zhang S.-L, Liu L., Fu Y., Guo Q.-X. Organometallics: 2007; 26 4546