Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis

European Journal of Organic Chemistry

Volumn , Issue 16, 2010, Pages 3027-3031

  Gutierrez, Elisa G ^a   Moorhead, Eric J ^a   Smith, Eva H ^a   Lin, Vivian ^a   Ackerman, Laura K G ^a   Knezevic, Claire E ^a   Sun, Victoria ^a   Grant, Sharday ^a   Wenzel, Anna G ^a  

^a SCRIPPS COLLEGE   (United States)

Author keywords

Asymmetric catalysis; Biaryls; Chiral resolution; Organocatalysis

Indexed keywords

EID: 77952587898     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000070     Document Type: Article

References (37)

1. For reviews on Brønsted acid catalysis, see: a) M. Terada, Chem. Commun. 2008 4097-4112;
2. b) T. Akiyama, Chem. Rev. 2007 707 5744-5758;
3. c) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006 348 999-1010, and references therein.
4. For preparative methods, see: a) J. Bao, W. D. Wulff, J. B. Dominy, M. J. Fumo, E. B. Grant, A. C. Rob, M. C Whitcomb, S.-M. Yeung, R. L. Ostrander, A. L. Rheingold, J. Am. Chem. Soc, 1996 118 3392-3405;
5. b) L. K. Truesdale, Org. Synth, 1989 67 13;
6. Org. Synth. Coll. Vol. 1993 8 46.
7. For examples of chiral phosphoric acids not derived from binaphthol, see: a) T. Akiyama, T. Katoh, K. Mori, K. Kanno, Synlett 2009 1664-1666;
8. b) J. Moreau, A. Duboc, C Hubert, J.-P. Hurvois, J.-L. Renaud, Tetrahedron Lett. 2007 48 86478650;
9. c) E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007 129 12084-12085;
10. d) G. Li, Y. Liang, J. C Antilla, J. Am. Chem. Soc. 2007 129 5830-5831;
11. e) M. Terada, K. Sorimachi, D. Uraguchi, Synlett 2006, 133-136;
12. f) T. Akiyama, Y Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005 347 1523-1526;
13. g) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005 727 15696-15697.
14. T. Akiyama, Y. Tamura, J. Itoh, H. Morita, K. Fuchibe, Angew. Chem. Int. Ed. 2004 43 1566-1568.
15. T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005 7 2583-2585.
16. R. I. Storer, D. E. Carrera, Y. Ni, D. W. C MacMillan, J. Am. Chem. Soc. 2006 128 84-86.
17. H.-Y. Tang, A.-D. Lu, Z.-H. Zhou, G.-F. Zhao, L.-N. He, C.C. Tang, Eur. J. Org. Chem. 2008 1406-1410.
18. R. R. Schrock, A. H. Hoveyda, Asymmetric Metathesis Reactions Involving Aehiral and Meso Substrates, PCT Int. Appl., 2000002834, Jan 20, 2000.
19. C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008 130 9246-9247.
20. For a review, see: P. Merino, E. Marques-Lopez, R. P. Herrera, Adv. Synth. Catal. 2008 350 1195-1208.
21. For organocatalytic, asymmetric versions, see: a) S. Nakamura, H. Nakashima, A. Yamamura, N. Shibata, T. Toru, Adv. Synth. Catal. 2008 350 1209-1212;
22. b) D. Pettersen, M. Marcolini, L. Bernardi, F. Fini, R. P. Herrera, V. Sgarzani, A. Ricci, J. Org. Chem. 2006 77 6269-6272;
23. c) G. D. Joly, E. N. Jacobsen, J. Am. Chem. Soc. 2004 126 4102-4103.
24. For organocatalytic, asymmetric versions, see: a) L.-W. Zhou, L. Xu, L. Li, C.-G. Yang, Eur. J. Org. Chem. 2006, 5225-5227;
25. b) W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007 5 816-821;
26. c) G. Bartoli, M. Bosco, A. Carlone, F. Pexciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007 9 1403-1405;
27. d) D.-P. Li, Y.-C. Guo, Y. Guo, W.-J. Xiao, Chem. Commun. 2006 799-801;
28. e) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002 124 1172-1173.
29. R. Singh, C. Czekelius, R. R. Schrock, P. Müller, A. H. Hoveyda, Organometallics 2007 26 2528-2529.
30. For references to adapted methods, see: a) P. J. Wallis, P. J. Booth, A. F. Patti, J. L. Scott, Green Chem. 2006 8 333-337;
31. b) S. Ji, J. Lu, X. Zhu, J. Yang, J. Lang, L. Wu, Synth. Commun. 2002 32 3069-3074;
32. c) K. Ding, Y. Wang, L. Zhang, Y. Wu, T. Matsuura, Tetrahedron 1996 52 1005-1010;
33. [2a,7]
34. The scope of this microwave protocol has been investigated and will be reported shortly.
35. See Supporting Information. CCDC-772003 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
36. F. A. Davis, S. Lee, H. Yan, D.D. Titus, Org. Lett. 2001 5 1757-1760.
37. W. Zhou, L.-W. Xu, L. Li, L. Yang, C.-G. Xia, Eur. J. Org. Chem. 2006 5225-5227.