Highly efficient and modularly tuned bicyclic organocatalyst for the enantioselective michael addition of aldehydes to nitroalkenes

Synthesis

Volumn , Issue 12, 2011, Pages 1912-1917

  Xiao, Jian ^a,b   Xu, Feng Xia ^a   Lu, Yun Peng ^a   Liu, Yan Ling ^a   Loh, Teck Peng ^a  

^a Nanyang Technological University   (Singapore)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

bicyclic; enamine control; Michael addition; organocatalyst

Indexed keywords

BICYCLIC; ENAMINES; ENANTIOSELECTIVE MICHAEL ADDITION; GOOD YIELD; MICHAEL ADDITIONS; NITROALKENES; ORGANOCATALYSTS;

ALDEHYDES; ENANTIOSELECTIVITY; ORGANIC COMPOUNDS;

ADDITION REACTIONS;

2 ETHYL 4 NITRO 3 PHENYLBUTANAL; 2 METHYL 3 (NAPHTHALEN 1 YL) 4 NITROBUTANAL; 2 METHYL 3 (NAPHTHALEN 2 YL) 4 NITROBUTANAL; 2 METHYL 4 NITRO 3 PHENYLBUTANAL; 3 (4 BROMOPHENYL) 2 METHYL 4 NITROBUTANAL; 3 (4 METHOXYPHENYL) 2 METHYL 4 NITROBUTANAL; 3 (FURAN 2 YL) 2 METHYL 4 NITROBUTANAL; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; NITROALKENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLOPROPANATION; ENANTIOSELECTIVITY; HYDROGEN BOND; MANNICH REACTION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 79958086117     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260527     Document Type: Article

References (58)

1. Berkessel A, Groger H, Asymmetric Organocatalysis Wiley-VCH Weinheim 2005
2. Enantioselective Organocatalysis Dalko P I. Wiley-VCH Weinheim 2007
3. Dalko P I., Moisan L, Angew. Chem. Int. Ed. 2004 43 5138
4. List B, Chem. Commun. 2006 819
5. Marigo M, Jrgensen K A., Chem. Commun. 2006 2001
6. Barbas C F. III, Angew. Chem. Int. Ed. 2008 47 42
7. Melchiorre P, Marigo M, Carlone A, Bartoli G, Angew. Chem. Int. Ed. 2008 47 6138
8. Mukherjee S, Yang J W., Hoffmann S, List B, Chem. Rev. 2007 107 5471
9. Bertelsen S, Jrgensen K A., Chem. Soc. Rev. 2009 38 2178
10. MacMillan D W. C., Nature 2008 455 304
11. Westermann B, Ayaz M, Berkel S, Angew. Chem. Int. Ed. 2010 49 846
12. Grondal C, Jeanty M, Enders D, Nat. Chem. 2010 2 167
13. For reviews, see:, List B, Tetrahedron 2002 58 5573
14. Movassaghi M, Jacobsen E N., Science 2002 298 1904
15. List B, Pojarliev P, Martin H J., Org. Lett. 2001 3 2423
16. Betancort J M., Barbas C F. III, Org. Lett. 2001 3 3737
17. Enders D, Seki A, Synlett 2002 26
18. Beeson T D., Mastracchio A, Hong J.-B, Ashton K, MacMillan D W. C., Science 2007 316 582
19. Jang H.-Y, Hong J.-B, MacMillan D W. C., J. Am. Chem. Soc. 2007 129 7004
20. Kim H, MacMillan D W. C., J. Am. Chem. Soc. 2008 130 398
21. Lelais G, MacMillan D W. C., Aldrichimica Acta 2006 39 79
22. For reviews, see
23. Palomo C, Mielgo A, Angew. Chem. Int. Ed. 2006 45 7876
24. Mielgo A, Palomo C, Chem. Asian J. 2008 3 922
25. Hayashi Y, Gotoh H, Hayashi T, Shoji M, Angew. Chem. Int. Ed. 2005 44 4212
26. Marigo M, Wabnitz T C., Fielenbach D, Jrgensen K A., Angew. Chem. Int. Ed. 2005 44 794
27. Marigo M, Fielenbach D, Braunton A, Kjasgaard A, Jrgensen K A., Angew. Chem. Int. Ed. 2005 44 3703
28. Franzén J, Marigo M, Fielenbach D, Wabnitz T C., Kjrsgaard A, Jrgensen A K., J. Am. Chem. Soc. 2005 127 18296
29. Xiao J, Lu Y P., Liu Y L., Wong P S., Loh T P., Org. Lett. 2011 13 876
30. Xiao J, Xu F X., Lu Y P., Loh T P., Org. Lett. 2010 12 1220
31. Xiao J, Wong Z Z., Lu Y P., Loh T P., Adv. Synth. Catal. 2010 352 1107
32. Xiao J, Loh T P., Org. Lett. 2009 11 2876
33. Xiao J, Liu Y L., Loh T P., Synlett 2010 2029
34. Xiao J, Loh T P., Synlett 2007 815
35. Xiao J, Loh T P., Tetrahedron Lett. 2008 49 7184
36. Kunz R K., MacMillan D W. C., J. Am. Chem. Soc. 2005 127 3240
37. Sakthivel K, Notz W, Bui T, Barbas C F. III, J. Am. Chem. Soc. 2001 123 5260
38. Luo R S., Weng J, Ai H B., Lu G, Chan A S. C., Adv. Synth. Catal. 2009 351 2449
39. Tang X, Liegault B, Renaud J.-L, Bruneau C, Tetrahedron: Asymmetry 2006 17 2187
40. Shinisha C B., Sunoj R B., Org. Biomol. Chem. 2007 5 1287
41. Pietruszka J, Simon R C., ChemCatChem 2010 2 505
42. Clarke M L., Fuentes J A., Angew. Chem. Int. Ed. 2007 46 930
43. Mandal T, Zhao C G., Angew. Chem. Int. Ed. 2008 47 7714
44. Gu L, Zhao G, Adv. Synth. Catal. 2007 349 1629
45. Zhang X J., Liu S P., Li X M., Yan M, Chan A S. C., Chem. Commun. 2009 833
46. Blackmond D G., Moran A, Hughes M, Armstrong A, J. Am. Chem. Soc. 2010 132 7598
47. For recent reviews, see
48. Mossé S, Alexakis A, Chem. Commun. 2007 3123
49. Berner O M., Tedeschi L, Enders D, Eur. J. Org. Chem. 2002 1877
50. Roca-Lopez D, Sadaba D, Delso I, Herrera R P., Tejero T, Merino P, Tetrahedron: Asymmetry 2010 21 2561
51. Mase N, Watanabe K, Yoda H, Takabe K, Tanaka F, Barbas C F. III, J. Am. Chem. Soc. 2006 128 4966
52. Hayashi Y, Gotoh H, Hayashi T, Shoji M, Angew. Chem. Int. Ed. 2005 44 4212
53. Wang W, Wang J, Li H, Angew. Chem. Int. Ed. 2005 44 1369
54. Palomo C, Vera S, Mielgo A, Gomez-Bengoa E, Angew. Chem. Int. Ed. 2006 45 5984
55. Zhu S, Yu S, Ma D, Angew. Chem. Int. Ed. 2008 47 545
56. Uehara H, Barbas C F. III, Angew. Chem. Int. Ed. 2009 48 9848
57. Seebach D, Beck A K., Golinski J, Hay J N., Laube T, Helv. Chim. Acta 1985 6 162
58. Seebach D, Golinski J, Helv. Chim. Acta 1981 64 1413