Organocatalytic enantioselective substitution of MBH carbonates by 2-fluoromalonates

Tetrahedron Letters

Volumn 53, Issue 32, 2012, Pages 4124-4129

  Wang, Bing ^a,b   Companyó, Xavier ^b   Li, Jing ^a   Moyano, Albert ^b   Rios, Ramon ^b,c  

^a NANKAI UNIVERSITY   (China)

^b UNIVERSITY OF BARCELONA   (Spain)

^c INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

Enantioselective; Fluorine; Lewis base; MBH carbonates; Organocatalysis

Indexed keywords

2 FLUOROMALONATE DERIVATIVE; CARBONIC ACID DERIVATIVE; LEWIS BASE; MALONIC ACID DERIVATIVE; MORITA BAYLIS HILLMAN CARBONIC ACID DERIVATIVE; ORGANOFLUORINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; ENANTIOSELECTIVITY;

EID: 84863621863     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.121     Document Type: Article

References (41)

1. For an excellent review of stereogenic formation of fluorinated compounds, see: D. Cahard, X. Xu, S. Couve-Bonnaire, and X. Pannecoucke Chem. Soc. Rev. 39 2010 558 568
2. P. Kirsh Modern Fluoroorganic Chemistry 2004 Wiley-VCH Weinheim, Germany
3. B.E. Smart J. Fluorine Chem. 109 2001 3 11
4. V.A. Soloshonok Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedical Targets 1999 Wiley-VCH Chichester, UK
5. R.E. Banks, and J.C. Smart Organofluorine Chemistry: Principles and Commercial Applications 1994 Plenum New York
6. R. Filler, Y. Kobayashi, and L.M. Yagupol'skii Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications 1993 Elsevier Amsterdam
7. T. Hiyama Organofluorine Compounds: Chemistry and Applications 2000 Springer Berlin
8. D. O'Hagan Chem. Soc. Rev. 37 2008 308 319
9. G.K.S. Prakash, and J. Hu Acc. Chem. Res. 40 2007 921 930
10. K. Miller, C. Faeh, and F. Diederich Science 317 2007 1881 1888
11. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
12. C. Isanbor, and D.J. O'Hagan J. Fluorine Chem. 127 2006 303 319
13. J.-P. Begué, and D. Bonnet-Delpon J. Fluorine Chem. 127 2006 992 1012
14. J. Kirk J. Fluorine Chem. 127 2006 1012 1029
15. H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, and M. Stahl ChemBioChem 5 2004 637 643
16. For a concise review on the organocatalytic synthesis of fluorinated compounds see: G. Valero, X. Companyó, and R. Rios Chem. Eur. J. 17 2011 2018 2037
17. D. Enders, and M.R.M. Huttl Synlett 2005 991 993
18. D.D. Steiner, N. Mase, and C.F. Barbas III Angew. Chem., Int. Ed. 44 2005 3706 3710
19. T.D. Beeson, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 8826 8828 For a nice tandem reaction with α-fluorination see
20. C. Appayee, and S.E. Brenner-Moyer Org. Lett. 12 2010 3356 3359
21. D.A. Nagib, M.E. Scott, and D.W.C. MacMillan J. Am. Chem. Soc. 131 2009 10875 10877
22. A.-N. Alba, X. Companyó, A. Moyano, and R. Rios Chem. Eur. J. 15 2009 7035 7038
23. S. Zhang, Y. Zhang, Y. Ji, and W. Wang Chem. Commun. 2009 4886 4888
24. F. Ullah, G.-L. Zhao, L. Deiana, M. Zhu, P. Dziedzic, I. Ibrahem, P. Hammar, J. Sun, and A. Cordova Chem. Eur. J. 15 2009 10013 10017
25. T. Furukawa, N. Shibata, S. Mizuta, S. Nakamura, T. Toru, and M. Shiro Angew. Chem., Int. Ed. 47 2008 8051 8054
26. For an example of malonate addition to MBH carbonates catalyzed by β-ICN see: Y. Du, X. Han, and X. Lu Tetrahedron Lett. 45 2004 4967 4971
27. W. Yang, X. Wei, Y. Pan, R. Lee, B. Zhu, H. Liu, L. Yan, K.-W. Huang, Z. Jiang, and C.-H. Tan Chem. Eur. J. 17 2011 8066 8070
28. T. Furukawa, J. Kawazoe, W. Zhang, T. Nishimine, E. Tokunaga, T. Matsumoto, M. Shiro, and N. Shibata Angew. Chem., Int. Ed. 50 2011 9684 9688
29. For a similar reaction leading to the trifluoromethylation of MBH carbonates see: T. Furukawa, T. Nishimine, E. Tokunaga, K. Hasegawa, M. Shiro, and N. Shibata Org. Lett. 13 2011 3972 3975
30. X. Companyó, G. Valero, V. Ceban, T. Calvet, M. Font-Bardia, A. Moyano, and R. Rios Org. Biomol. Chem. 9 2011 7986 7989 For a review about the organocatalytic methodologies of MBH carbonates see
31. R. Rios Catal. Sci. Technol. 2 2012 267 278
32. X. Companyó, M. Hejnová, M. Kamlar, J. Veselý, A. Moyano, and R. Rios Tetrahedron Lett. 50 2009 5021 5024
33. G. Valero, A.-N. Balaguer, A. Moyano, and R. Rios Tetrahedron Lett. 49 2008 6559 6562
34. X. Companyó, G. Valero, L. Crovetto, A. Moyano, and R. Rios Chem. Eur. J. 15 2009 6564 6568
35. X. Companyó, A.-N. Balaguer, F. Cárdenas, A. Moyano, and R. Rios Eur. J. Org. Chem. 2009 3075 3080
36. A.-N.R. Alba, X. Companyó, G. Valero, A. Moyano, and R. Rios Chem. Eur. J. 16 2010 5354 5361
37. A.-N.R. Alba, G. Valero, T. Calvet, M. Font-Bardia, A. Moyano, and R. Rios Chem. Eur. J. 16 2010 9884 9889
38. X. Companyó, A. Zea, A.-N.R. Alba, A. Mazzanti, A. Moyano, and R. Rios Chem. Commun. 46 2010 6953 6955
39. G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, and R. Rios Tetrahedron Lett. 50 2009 1943 1946
40. A.N. Alba, X. Companyo, A. Moyano, and R. Rios Chem. Eur. J. 15 2009 11095 11099
41. S.D.J.V.C. Van Steenis, T. Marcelli, M. Lutz, A.L. Spek, H. van, and M.J.H. Hiemstra Adv. Synth. Catal. 349 2007 281 286