Highly efficient synthesis of spirocyclic (1R)-camphor-derived triazolium salts: Application in the catalytic asymmetric benzoin condensation

Tetrahedron

Volumn 70, Issue 35, 2014, Pages 5739-5745

  Rafiński, Zbigniew ^a   Kozakiewicz, Anna ^a   Rafińska, Katarzyna ^a  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

Asymmetric synthesis; Benzoin condensation; N Heterocyclic carbenes; Terpenoids

Indexed keywords

ALDEHYDE; BENZOIN; CAMPHOR DERIVATIVE; INORGANIC SALT; KETOL;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; COMPARATIVE STUDY; DIMERIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGEN BOND; OPTICAL ROTATION; PRIORITY JOURNAL; SYNTHESIS;

DRYOBALANOPS;

EID: 84949117053     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.06.066     Document Type: Article

References (46)

1. D. Enders, T. Balensiefer, O. Niemeier, and M. Christmann P.I. Dalko, Enantioselective Organocatalysis: Reactions and Experimental Procedures 2007 Wiley-VCH Weinheim, Germany 331 355
2. D. Enders, O. Niemeier, and A. Henseler Chem. Rev. 107 2007 5606
3. J.L. Moore, and T. Rovis Top. Curr. Chem. 291 2009 77
4. P.-C. Chiang, and J.W. Bode S. Díez-González, N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools 2010 Royal Society of Chemistry Cambridge, United Kingdom 339 445
5. C.D. Campbell, K.B. Ling, and A.D. Smith C.S.J. Cazin, N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis Vol. 32 2011 Springer Dortrecht, Germany 263 297
6. X. Bugaut, and F. Glorius Chem. Soc. Rev. 41 2012 3511
7. J.S. Johnson Angew. Chem., Int. Ed. 43 2004 1326
8. D. Enders, and T. Balensiefer Acc. Chem. Res. 37 2004 534
9. K. Zeitler Angew. Chem., Int. Ed. 44 2005 7506
10. M. Christmann Angew. Chem., Int. Ed. 44 2005 2632
11. N. Marion, S. Díez-González, and S.P. Nolan Angew. Chem., Int. Ed. 46 2007 2988
12. V. Nair, S. Vellalath, and B.P. Babu Chem. Soc. Rev. 37 2008 2691
13. J. Read de Alaniz, and T. Rovis Synlett 2009 1189
14. E.M. Phillips, A. Chan, and K.A. Scheidt Aldrichimica Acta 42 2009 55
15. A.T. Biju, N. Kuhl, and F. Glorius Acc. Chem. Res. 44 2011 1182
16. K. Hirano, I. Piel, and F. Glorius Chem. Lett. 40 2011 786
17. P.-C. Chiang, and J.W. Bode TCIMail 149 2011 2
18. H.U. Vora, and T. Rovis Aldrichimica Acta 44 2011 3
19. Z.-Q. Rong, W. Zhang, G.-Q. Yang, and S.-L. You Curr. Org. Chem. 15 2011 3077
20. D.T. Cohen, and K.A. Scheidt Chem. Sci. 3 2012 53
21. A. Grossmann, and D. Enders Angew. Chem., Int. Ed. 51 2012 314
22. T. Rovis, and C. Filloux E.M. Carreira, H. Yamamoto, Comprehensive Chirality Vol. 6 2012 Elsevier Ltd Amsterdam 318 344
23. H.U. Vora, P. Wheeler, and T. Rovis Adv. Synth. Catal. 354 2012 1617
24. F. Wöhler, and Liebig J. Ann. Pharm. 3 1832 249
25. T. Ukai, S. Tanaka, and S. Dokawa J. Pharm. Soc. Jpn. 63 1943 269
26. R. Breslow J. Am. Chem. Soc. 80 1958 3719
27. J.C. Sheehan, and D.H. Hunnemann J. Am. Chem. Soc. 88 1966 3666
28. J.C. Sheehan, and T. Hara J. Org. Chem. 39 1974 1196
29. D. Enders, K. Breuer, and J.H. Teles Helv. Chim. Acta 79 1996 1217
30. R.L. Knight, and F.J. Leeper J. Chem. Soc., Perkin Trans. 1 1998 1891
31. D. Enders, and U. Kallfass Angew. Chem., Int. Ed. 41 2002 1743
32. D. Enders, and J. Han Tetrahedron: Asymmetry 19 2008 1367
33. L. Baragwanath, C.A. Rose, K. Zeitler, and S.J. Connon J. Org. Chem. 74 2009 9214
34. Z. Rafiński, A. Kozakiewicz, and K. Rafińska ACS Catal. 4 2014 1404
35. S. Ye, Z.-Z. Huang, C.-A. Xia, Y. Tang, and L.-X. Dai J. Am. Chem. Soc. 124 2002 2432
36. M. Kitamura, H. Oka, S. Suga, and R. Noyori Org. Synth. 79 2003 139
37. H.Y. Kim, A.E. Lurain, P. García-García, P.J. Carroll, and P.J. Walsh J. Am. Chem. Soc. 127 2005 13138
38. R.J. Kloetzing, T. Thaler, and P. Knochel Org. Lett. 8 2006 1125
39. X.-M. Deng, P. Cai, S. Ye, X.-L. Sun, W.-W. Liao, K. Li, Y. Tang, Y.-D. Wu, and L.-X. Dai J. Am. Chem. Soc. 128 2006 9730
40. H.S. Wilkinson, P.T. Grover, C.P. Vandenbossche, R.P. Bakale, N.N. Bhongle, S.A. Wald, and C.H. Senanayake Org. Lett. 3 2001 553
41. J.R. Struble, and J.W. Bode Org. Synth. 87 2010 362
42. C.J. Collett, R.S. Massey, O.R. Maguire, A.S. Batsanov, A.C. O'Donoghue, and A.D. Smith Chem. Sci. 4 2013 1514
43. S.E. O'Toole, and S.J. Connon Org. Biomol. Chem. 7 2009 3584
44. G.M. Sheldrick SHELXS97 and SHELXL97 1997 University of Göttingen Germany
45. H.D. Flack Acta Crystallogr., Sect. A 39 1983 876
46. T. Soeta, Y. Tabatake, K. Inomata, and Y. Ukaji Tetrahedron 68 2012 894