Organocatalytic asymmetric wittig reactions: Generation of enantioenriched axially chiral olefins breaking a symmetry plane

Synlett

Volumn , Issue 18, 2011, Pages 2745-2749

  Gramigna, Lucia ^a   Duce, Sara ^a,b   Filippini, Giacomo ^a   Fochi, Mariafrancesca ^a   Franchini, Mauro Comes ^a   Bernardi, Luca ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

asymmetric catalysis; chirality; olefination; Wittig reaction; ylides

Indexed keywords

ALKENE DERIVATIVE; CYCLOHEXANONE; PHOSPHORUS;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; CYCLOADDITION; ENANTIOMER; HORNER WADSWORTH EMMONS REACTION; HYDROGEN BOND; MOLECULAR STABILITY; OLEFINATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; WITTIG REACTION; WITTIG REARRANGEMENT;

EID: 80455122760     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289516     Document Type: Article

References (58)

1. Reviews: Enantioselective Organocatalysis Dalko P I. Wiley-VCH Weinheim 2007
2. Asymmetric Organocatalysis List B Springer Berlin 2009
3. Special issue on organocatalysis:, List B (Ed.), Chem. Rev. 2007 107 5413
4. Eliel E, Stereochemistry of Organic Compounds Wiley-Interscience New York 1994
5. Bringmann G, Gulder T, Gulder T A. M., Breuning M, Chem. Rev. 2011 111 563
6. Hoffmann-Röder A, Krause N, Angew. Chem. Int. Ed. 2004 43 1196
7. Noyori R, Angew. Chem. Int. Ed. 2002 41 2008
8. Brunel J M., Chem. Rev. 2005 105 857
9. Akiyama T, Chem. Rev. 2007 107 5744
10. Terada M, Synthesis 2010 1929
11. Fu G C., Acc. Chem. Res. 2004 37 542
12. Curran D P., Qi H, Geib S J., DeMello N C., J. Am. Chem. Soc. 1994 116 3131
13. Ma S, Chem. Rev. 2005 105 2829
14. Koumura N, Zijlstra L W. J., vanDelden L A., Harada N, Feringa B L., Nature (London) 1999 401 152
15. For exceptions, see:, Brandes S, Bella M, Kjærsgaard A, Jørgensen K A., Angew. Chem. Int. Ed. 2006 45 1147
16. Liu H, Leow D, Huang K.-W, Tan C.-H, J. Am. Chem. Soc. 2009 131 7212
17. Gustafson J L., Lim D, Miller S J., Science 2010 328 1251
18. Cozzi P G., Emer E, Gualandi A, Angew. Chem. Int. Ed. 2011 50 3847
19. Wittig G, Geissler G, Justus Liebigs Ann. Chem. 1953 580 44
20. Horner L, Hoffmann H, Wippel H G., Chem. Ber. 1958 91 61
21. Horner L, Hoffmann H, Wippel H G., Klahre G, Chem. Ber. 1959 92 2499
22. Wadsworth W S. Jr., Emmons W D., J. Am. Chem. Soc. 1961 83 1733.
23. Maryanoff B E., Reitz A B., Chem. Rev. 1989 89 863
24. OBrien C J., Tellez J L., Nixon Z S., Kang L J., Carter A L., Kunkel S R., Przeworski K C., Chass G A., Angew. Chem. Int. Ed. 2009 48 6836
25. Dong D.-J, Li H.-H, Tian S.-K, J. Am. Chem. Soc. 2010 132 5018
26. Reviews:, Brummond K M., DeForrest J E., Synthesis 2007 795
27. Hoffmann-Röder A, Krause N, Angew. Chem. Int. Ed. 2002 41 2933
28. Rein T, Pedersen T M., Synthesis 2002 579
29. Li A.-H, Dai L.-X, Aggarwal V K., Chem. Rev. 1997 97 2341
30. Bestmann H J., Lienert J, Angew. Chem., Int. Ed. Engl. 1969 8 763
31. Hanessian S, Delorme D, Beaudoin S, Leblanc Y, J. Am. Chem. Soc. 1984 106 5754
32. Denmark S E., Chen C.-T, J. Am. Chem. Soc. 1992 114 10674
33. Mizuno M, Fuji K, Tomioka K, Angew. Chem. Int. Ed. 1998 37 515
34. Li C.-Y, Wang X.-B, Sun X.-L, Tang Y, Zheng J.-C, Xu Z.-H, Zhou Y.-G, Dai L.-X, J. Am. Chem. Soc. 2007 129 1494
35. Li C.-Y, Sun X.-L, Jing Q, Tang Y, Chem. Commun. 2006 2980
36. PinhoeMelo T M. V. D., Cardoso A L., RochaGonsalves A M. dA, Pessoa J C., Paixão J A., Beja A M., Eur. J. Org. Chem. 2004 4830
37. Hanessian S, Beaudoin S, Tetrahedron Lett. 1992 33 7659
38. Suarez M, Schuster G B., J. Am. Chem. Soc. 1995 117 6732
39. Arai S, Hamaguchi S, Shioiri T, Tetrahedron Lett. 1998 39 2997
40. Ramachary D B., Barbas C F. III., Org. Lett. 2005 7 1577
41. Li L, Seidel D, Org. Lett. 2010 12 5064; and references therein
42. Jiang H, Halskov K S., Johansen T K., Jørgensen K A., Chem. Eur. J. 2011 17 3842
43. Vedejs E, Peterson M J., Top. Stereochem. 1994 21 1
44. Robiette R, Richardson J, Aggarwal V K., Harvey J N., J. Am. Chem. Soc. 2006 128 2394; and references cited therein
45. Reviews on hydrogen-bond organocatalysis:, Taylor M, Jacobsen E N., Angew. Chem. Int. Ed. 2006 45 1520
46. Zhang Z, Schreiner P, Chem. Soc. Rev. 2009 38 1187
47. Gung B W., Chem. Rev. 1999 99 1377
48. Acceleration of the Wittig reaction in alcoholic solvents has been reported. See for example:, Rüchardt C, Panse P, Eichler S, Chem. Ber. 1967 100 1144
49. Albrecht, Albrecht A, Krawczyk H, Jørgensen K A., Chem. Eur. J. 2010 16 28
50. Zhang Y, Liu Y.-K, Kang T.-R, Hu Z.-K, Chen Y.-C, J. Am. Chem. Soc. 2008 130 2456
51. Hong B.-C, Jan R.-H, Tsai C.-W, Nimje R Y., Liao J.-H, Lee G.-H, Org. Lett. 2009 11 5246
52. Mazzotta S, Gramigna L, Bernardi L, Ricci A, Org. Process Res. Dev. 2010 14 687
53. Sohtome Y, Tanatani A, Hashimoto Y, Nagasawa K, Tetrahedron Lett. 2004 45 5589
54. Seebach D, Beck A K., Heckel A, Angew. Chem. Int. Ed. 2001 40 92
55. Huang Y, Unni A K., Thadani A N., Rawal V H., Nature (London) 2003 424 146
56. Toda F, Akai H, J. Org. Chem. 1990 55 3446
57. Cid M B., Duce S, Morales S, Rodrigo E, GarcíaRuano J L., Org. Lett. 2010 12 3586
58. Giese B, Schoch J, Rüchardt C, Chem. Ber. 1978 111 1395