A new microwave-assisted organocatalytic solvent-free synthesis of optically enriched Michael adducts

Synlett

Volumn , Issue 12, 2010, Pages 1849-1853

  Procopio, Antonio ^a   De Nino, Antonio ^b   Nardi, Monica ^b   Oliverio, Manuela ^a   Paonessa, Rossella ^a   Pasceri, Raffaele ^a  

^a UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^b UNIVERSITY OF CALABRIA   (Italy)

Author keywords

asymmetric catalysis; enones; green chemistry; homogeneous catalysis; Michael reaction

Indexed keywords

2 CYCLOHEXENONE; DIETHYLMALONIC ACID; MALONIC ACID DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; MICHAEL ADDITION; MICROWAVE RADIATION; ORGANIC CHEMISTRY; REPRODUCIBILITY; SOLVENT EFFECT;

EID: 77954849793     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258126     Document Type: Article

References (54)

1. (a) MacMillan D W. C., Nature (London) 2008 455 304
2. (b) Dalko P I., Moisan L, Angew. Chem. Int. Ed. 2001 40 3726
3. (c) Dalko P I., Moisan L, Angew. Chem. Int. Ed. 2004 43 5138
4. (d) Berkessel A, Groöger H, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis Wiley-VCH Weinheim 2005
5. (e) List B, Chem. Commun. 2006 819
6. (f) Marcelli T, vanMaarseveen J H., Hiemstra H, Angew. Chem. Int. Ed. 2006 45 7496
7. (g) Palomo C, Mielgo A, Angew. Chem. Int. Ed. 2006 45 7876
8. (h) Enders D, Grondal C, Hüttl M R. M., Angew. Chem. Int. Ed. 2007 46 1570
9. (a) Enders D, Hüttl M R. M., Grondal C, Raabe G, Nature (London) 2006 441 861
10. (b) Seayed J, List B, Org. Biomol. Chem. 2005 3 719
11. (a) Notz W, List B, J. Am. Chem. Soc. 2000 122 7386
12. (b) Sakthivel K, Notz W, Bui T, Barbas C F. III, J. Am. Chem. Soc. 2001 123 5260
13. (c) Pidathala C, Hoang L, Vignola N, List B, Angew. Chem. Int. Ed. 2003 42 2785
14. (d) List B, Acc. Chem. Res. 2004 37 548
15. (e) Notz W, Tanaka F, Barbas C F. III, Acc. Chem. Res. 2004 37 580
16. (f) Notz W, Watanabe S.-I, Chowdari N S., Zhong G, Betancort J M., Tanaka F, Barbas C F. III, Adv. Synth. Catal. 2004 346 1131
17. Sheldon R A., Arenders I, Hanefeld U, Green Chemistry and Catalysis Wiley-VCH Weinheim 2007
18. Pellissier H, Tetrahedron 2007 63 9267
19. Brandau S, Landa A, Franze J, Marigo M, Jrgensen K A., Angew. Chem. Int. Ed. 2006 45 4305
20. (a) Perlmutter A, Conjugative Additions in Organic Synthesis Pergamon Press Oxford 1992
21. (b) Yamaguchi M, Conjugate Addition of Stabilized Carbanions, In Comprehensive Asymmetric Catalysis Vol. 3 Jacobsen [nl]E N. Pfaltz A Yamamoto H Springer Berlin 1999
22. (c) Sibi M P., Manyem S, Tetrahedron 2000 56 8033
23. (d) Krause N, Hoffmann-Röder A, Synthesis 2001 171
24. (a) Walsh P J., Li H, AnayadeParrodi C, Chem. Rev. 2007 107 2503
25. (b) DeSimone J M., Science 2002 297 799
26. (c) Anastas P T., Williamson T C., Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes Oxford Science Publications New York 1998
27. (a) Sheldon R A., Chem. Ind. 1992 903
28. (b) Jacobsen [nl]E N., Finney N S., Chem. Biol. 1994 1 85
29. (a) Cave G W. V., Raston C L., Scott J L., Chem. Commun. 2001 2159
30. (b) Sheldon R A., Pure Appl. Chem. 2000 72 1233
31. (a) Metzger J O., Angew. Chem. Int. Ed. 1998 37 2975
32. (b) Tanaka K, Toda F, Chem. Rev. 2000 100 1025
33. (c) Tanaka K, Solvent-Free Organic Synthesis Wiley-VCH Weinheim 2003
34. Zhou J, Ye M C., Huang Z, Tang Y, J. Org. Chem. 2004 69 1309
35. (a) Almai D, Alonso D A., Gómez-Bengoa E, Nagel Y, Nájera C, Eur. J. Org. Chem. 2007 2328
36. (b) Ballini R, Bosica G, Fiorini D, Palmieri A, Petrini M, Chem. Rev. 2005 105 933
37. (a) Procopio A, Gaspari M, Nardi M, Oliverio M, Tagarelli A, Sindona G, Tetrahedron Lett. 2007 48 8623
38. (b) Procopio A, Gaspari M, Nardi M, Oliverio M, Romeo R, Tetrahedron Lett. 2008 49 1961
39. Sulzer-Mossé S, Alexakis A, Chem. Commun. 2007 3123
40. Mossé S, Alexakis A, Org. Lett. 2006 8 3577
41. Westermann B, Neuhaus C, Angew. Chem. Int. Ed. 2005 44 4077
42. Rodríguez B, Bolm C, J. Org. Chem. 2006 71 2888
43. (a) Hosseini M, Stiasni N, Barbieri V, Kappe C O., [nl]J. Org. Chem. 2007 72 1417
44. (b) Marigo M, Jorgensen K A., Chem. Commun. 2006 2001
45. (c) Connon S J., Chem. Eur. J. 2006 12 5419
46. (a) Larhed M, Moberg C, Hallberg A, Acc. Chem. Res. 2002 35 717
47. (b) Kappe C O., Angew. Chem. Int. Ed. 2004 43 6250
48. (c) delaHoz A, Díaz-Ortiz A, Moreno A, Chem. Soc. Rev. 2005 34 164
49. (d) Roberts B A., Strauss C R., Acc. Chem. Res. 2005 38 653
50. (e) Kappe C O., Stadler A, Microwaves in Organic and Medicinal Chemistry Wiley-VCH Weinheim 2005
51. (f) Tiernay J P., Lidström P, Microwave-Assisted Organic Synthesis Blackwell Oxford 2005
52. (g) Perreux L, Loupy A, Microwaves in Organic Synthesis 2nd ed Loupy A Wiley-VCH Weinheim 2006
53. Perreux L, Loupy A, Tetrahedron 2001 57 9199
54. Knudsen K R., Mitchell C E. T., Ley S V., Chem. Commun. 2006 66