Binap-gold(I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1,3-dipolar cycloaddition of azomethine ylides

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1184-1186

  Martín Rodríguez, María ^a   Nájera, Carmen ^a   Sansano, José M ^a   Wu, Feng Liu ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; BINAP GOLD(I) TRIFLUOROACETATE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 77956697078     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.06.011     Document Type: Article

References (28)

1. Special issue on coinage metals: Lipshutz, B. H; Yamamoto, Y. Eds. Chem. Rev. 2008, 108, 2793-3442.
2. P. Karoyan, S. Sagan, O. Lequin, J. Quancard, S. Lavielle, and G. Chassaing Targets Heterocycl. Syst. 8 2004 216 273
3. C. Nájera, and J.M. Sansano Chem. Rev. 107 2007 4273 4303
4. M.I. Calaza, and C. Cativiela Eur. J. Org. Chem. 2008 3427 3448
5. For recent reviews, see: C. Nájera, J.M. Sansano, and M. Yus J. Braz. Chem. Soc. 21 2010 377 412
6. Nájera, C.; Sansano, J. M. Topics Heterocyclic Chem., Ed. Hassner, A. 2008, 12, 117-146.
7. L.M. Stanley, and M.P. Sibi Chem. Rev. 108 2008 2887 2902
8. M. Álvarez-Corral, M. Muñoz-Dorado, and I. Rodríguez-García Chem. Rev. 108 2008 3174 3198
9. M. Naodovic, and H. Yamamoto Chem. Rev. 108 2008 3132 3148
10. V. Nair, and T.D. Suja Tetrahedron 63 2007 12247 12275
11. G. Pandey, P. Banerjee, and S.R. Gadre Chem. Rev. 106 2006 4484 4517
12. T.M.V.D. Pinho e Melo Eur. J. Org. Chem. 2006 2873 2888
13. M. Bonin, A. Chauveau, and L. Micouin Synlett 2006 2349 2363
14. C. Nájera, and J.M. Sansano Angew. Chem., Int. Ed. 44 2005 6272 6276
15. S. Husinec, and V. Savic Tetrahedron: Asymmetry 16 2005 2047 2061
16. R.A. Widenhoefer Chem. Eur. J. 14 2008 5381 5382
17. A.D. Melhado, M. Luparia, and F.D. Toste J. Am. Chem. Soc. 129 2007 12638 12639
18. J.M. Longmire, B. Wang, and X. Zhang J. Am. Chem. Soc. 124 2002 13400 13401
19. C. Nájera, M.G. Retamosa, and J.M. Sansano Org. Lett. 9 2007 4025 4028
20. C. Nájera, M.G. Retamosa, J.M. Sansano, A. de Cózar, and F.P. Cossío Tetrahedron: Asymmetry 19 2008 2913 2923
21. M. Martín-Rodríguez, C. Nájera, J.M. Sansano, P.R.R. Costa, E. Crizanto de Lima, and A.G. Dias Synlett 2010 962 966
22. C.A. Wheaton, M.C. Jennings, and R.J. Puddephatt J. Am. Chem. Soc. 128 2006 15370 15371
23. C.A. Wheaton, M.C. Jennings, and R.J. Puddephatt Z. Naturforsch., B: J. Chem. Sci. 64 2009 1469 1477
24. For recent reviews about multifunctional catalysis see: M. Shibasaki, M. Kanai, and S. Matsunaga Aldrichimica Acta 39 2006 31 39
25. M. Kanai, N. Kato, E. Ichikawa, and M. Shibasaki Pure Appl. Chem. 77 2005 2047 2052
26. M. Kanai, N. Kato, E. Ichikawa, and M. Shibasaki Synlett 2005 1491 1508
27. J.-M. Ma, and D. Cahard Angew. Chem., Int. Ed. 43 2004 4566 4583
28. a)-BinapAuTFA complexes: To a solution of the in situ prepared chiral gold complex (0.05 mmol, 46 mg) in toluene (2 mL) was added at room temperature a solution of the iminoester (0.5 mmol) and dipolarophile (0.5 mmol) in toluene (2 mL). In some cases DIPEA (0.05 mmol, 14 μL) was added (see Tables) and the mixture was stirred at room temperature for 16-48 h (see Tables) The reaction was filtered off and the organic filtrate was directly evaporated and the residue was purified by recrystallization or by flash chromatography yielding pure endo-cycloadducts 2, 4, or 5.