First example of highly stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes via chiral selenonium ylides

Chemistry - A European Journal

Volumn 15, Issue 15, 2009, Pages 3784-3789

  Wang, Hai Yang ^a   Yang, Fei ^a   Li, Xin Liang ^b   Yan, Xue Ming ^a   Huang, Zhi Zhen ^a  

^a NANJING UNIVERSITY   (China)

^b Basilea Pharmaceutica China Ltd   (China)

Author keywords

Chiral selenides; Cyclopropanation; Diastereoselectivity; Enantioselectivity; Ylides

Indexed keywords

CHIRAL SELENIDES; CYCLOPROPANATION; DIASTEREOSELECTIVITY; GOOD YIELDS; HIGH ENANTIOSELECTIVITIES; NEW STRATEGIES; RECYCLABILITY; STEREO-SELECTIVE SYNTHESIS; YLIDES;

ELECTRON TRANSITIONS; PROPANE; SELENIUM COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY;

ENANTIOSELECTIVITY;

CYCLOPROPANE DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYCLOPROPANES; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS; STEREOISOMERISM;

EID: 63849338847     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801936     Document Type: Article

References (31)

1. a) E. Piers, in Comprehensive Organic Synthesis, Vol. 5 (Ed.: B.M. Trost), Pergamon Press, Oxford, 1991, pp. 971;
2. b) Z. Rappoport, The Chemistry of the Cyclopropyl Group, Vol. 2, Wiley, New York, 1995;
3. c) J. Pietruszka, Chem. Rev. 2003, 103, 1051;
4. d) J. E. Baldwin, Chem. Rev. 2003, 103, 1197.
5. a) H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977;
6. b) P. Müller, Acc. Chem. Res. 2004, 37, 243;
7. c) G. Maas, Chem. Soc. Rev. 2004, 33, 183.
8. a) A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341;
9. b) E. M. McGarrigle, E. L. Myers, O. Ilia, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841.
10. a) V. K. Aggarwal, H. W. Smith, G. Hynd, R. V. H. Jones, R. Fieldhouse, S. E. Spey, J. Chem. Soc. Perkin Trans. 1 2000, 3267;
11. b) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482;
12. Angew. Chem. Int. Ed. 2001, 40, 1433.
13. R. Kunz, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240.
14. a) S. Ye, Z.-Z. Huang, C.-A. Xia, Y. Tang, L.-X. Dai, J. Am. Chem. Soc. 2002, 124, 2432;
15. b) X.-M. Deng, P. Cai, S. Ye, X.-L. Sun, W.-W. Liao, K. Li, Y. Tang, Y.-D. Wu, L.-X. Dai, J. Am. Chem. Soc. 2006, 128, 9730;
16. c) K. Huang, Z.-Z. Huang, Synlett 2005, 1621;
17. d) W.-W. Liao, K. Li, Y. Tang, J. Am. Chem. Soc. 2003, 125, 13030;
18. e) J.-C. Zheng, W.-W. Liao, Y. Tang, X.-L. Sun, L.-X. Dai, J. Am. Chem. Soc. 2005, 127, 12222.
19. a) W. W. Lote, J. Gosselck, Tetrahedron 1973, 29, 917;
20. b) T. Ibata, M. Kashiuchi, Bull. Chem. Soc. Jpn. 1986, 59, 929.
21. a) H. J. Reich, J. M. Renga, I. L. Reich, J. Am. Chem. Soc. 1975, 97, 5434;
22. b) R. J. Goodridge, T.W. Hambley, R. K. Haynes, D. D. Ridley, J. Org. Chem. 1988, 53, 2881;
23. c) X.-L. Li, Y. Wang, Z.-Z. Huang, Aust. J. Chem. 2005, 58, 749;
24. d) A.-H. Li, L.-X. Dai, X.-L. Hou, Y.-Z. Huang, F.-W. Li, J. Org. Chem. 1996, 61, 489.
25. CCDC 696520 (6a), 697353 (7) and 698747 (12) contain 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
26. a) K. Julienne, P. Metzner, J. Org. Chem. 1998, 63, 4532;
27. b) J. Zanardi, C. Leriverend, D. Aubert, K. Julienne, P. Metzner, J. Org. Chem. 2001, 66, 5620;
28. c) H. Takada, P. Metzner, C. Philouze, Chem. Commun. 2001, 2350;
29. d) J. F. Brière, H. Takada, P. Metzner, Phosphorus Sulfur Silicon Relax. Elem. 2005, 180, 965;
30. e) W.-H. Ou, Z.-Z. Huang, Synthesis 2005, 17, 2857.
31. For details see Supporting Information.