Effects of a flexible alkyl chain on an imidazole ligand for copper-catalyzed mannich reactions of terminal alkynes

Synlett

Volumn , Issue 20, 2010, Pages 3053-3056

  Okamura, Takaaki ^a   Asano, Keisuke ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

alkyl chain; copper; imidazole; Mannich reaction; steric effect

Indexed keywords

ALKYNE; COPPER; FORMALDEHYDE; IMIDAZOLE DERIVATIVE; PHENYLACETYLENE; PIPERIDINE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 78650175371     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259069     Document Type: Article

References (54)

1. Israelachvili J N., Mitchell D J., Ninham B W., [nl] J. Chem. Soc., Faraday Trans. 2 1976 72 1525
2. Holbrey J D., Seddon K R., J. Chem. Soc., Dalton Trans. 1999 2133
3. Asano K, Matsubara S, Org. Lett. 2010 12 4988
4. Malcolmson S J., Meek S J., Sattely E S., Schrock R R., Hoveyda A H., Nature (London) 2008 456 933
5. Asano K, Matsubara S, Org. Lett. 2009 11 1757
6. Asano K, Matsubara S, Synlett 2009 35
7. Asano K, Matsubara S, Synthesis 2009 3219
8. Güntensperger M, Zuberbühler A D., Helv. Chim. Acta 1977 60 2584
9. Asano K, Matsubara S, Heterocycles 2010 80 989
10. Copper(I)-imidazole systems have been well studied and shown to form a stable complex with an affinity for -acceptor compounds, see:, Kitagawa S, Munakata M, Bull. Chem. Soc. Jpn. 1986 59 2743
11. Kitagawa S, Munakata M, Bull. Chem. Soc. Jpn. 1986 59 2751
12. Gaykema W P. J., Hol W G. J., Vereijken J M., Soeter N M., Bak H J., Beintema J J., Nature (London) 1984 309 23
13. Linzen B, Soeter N M., Riggs A F., Schneider H.-J, Schartau W, Moore M D., Yokota E, Behrens P Q., Nakashima H, Takagi T, Nemoto T, Vereijken J M., Bak H J., Beintema J J., Volbeda A, Gaykema W P. J., Hol W G. J., Science 1985 229 519
14. Hayashi Y, Aratake S, Okano T, Takahashi J, Sumiya T, Shoji M, Angew. Chem. Int. Ed. 2006 45 5527
15. Mase N, Nakai Y, Ohara N, Yoda H, Takabe K, Tanaka F, Barbas C F. III., J. Am. Chem. Soc. 2006 128 734
16. Manabe K, Sun X.-M, Kobayashi S, J. Am. Chem. Soc. 2001 123 10101
17. Mannich C, Chang F T., Ber. Dtsch. Chem. Ges. 1933 66 418
18. Tramontini M, Synthesis 1973 703
19. Tramontini M, Angiolini L, Tetrahedron 1990 46 1791
20. Karlén B, Lindeke B, Lindgren S, Svensson K.-G, Dahlbom R, Jenden D J., Giering J E., J. Med. Chem. 1970 13 651
21. Simon D Z., Salvador R L., Champagne G, J. Med. Chem. 1970 13 1249
22. Adams T C., Dupont A C., Carter J P., Kachur J F., Guzewska M E., Rzeszotarski W J., Farmer S G., Noronha-Blob L, Kaiser C, J. Med. Chem. 1991 34 1585
23. Nilsson B M., Vargas H M., Ringdahl B, Hacksell U, J. Med. Chem. 1992 35 285
24. Sanders K B., Thomas A J., Pavia M R., Davis R E., Coughenour L L., Myers S L., Fisher S, Moos W H., Bioorg. Med. Chem. Lett. 1992 2 803
25. Musso D L., Clarke M J., Kelley J L., Boswell G E., Chen G, Org. Biomol. Chem. 2003 1 498
26. Hattori K, Miyata M, Yamamoto H, J. Am. Chem. Soc. 1993 115 1151
27. Boys M L., Tetrahedron Lett. 1998 39 3449
28. Craig J C., Ekwuribe N N., Tetrahedron Lett. 1980 21 2587
29. Nakamura H, Kamakura T, Ishikura M, Biellman J.-F, J. Am. Chem. Soc. 2004 126 5958
30. Nakamura H, Ishikura M, Sugiishi T, Kamakura T, Biellman J.-F, Org. Biomol. Chem. 2008 6 1471
31. Tabei J, Nomura R, Masuda T, Macromolecules 2002 35 5405
32. Gao G, Sanda F, Masuda T, Macromolecules 2003 36 3932
33. Crabbé P, Fillion H, André D, Luche J.-L, J. Chem. Soc., Chem. Commun. 1979 859
34. Kuang J, Ma S, J. Org. Chem. 2009 74 1763
35. Kuang J, Ma S, J. Am. Chem. Soc. 2010 132 1786
36. Ohno H, Ohta Y, Oishi S, Fujii N, Angew. Chem. Int. Ed. 2007 46 2295
37. Suzuki Y, Ohta Y, Oishi S, Fujii N, Ohno H, J. Org. Chem. 2009 74 4246
38. Ohta Y, Kubota Y, Watabe T, Chiba H, Oishi S, Fujii N, Ohno H, J. Org. Chem. 2009 74 6299
39. Kabalka G W., Wang L, Pagni R M., Synlett 2001 676
40. Sharifi A, Farhangian H, Mohsenzadeh F, Naimi-Jamal M R., Monatsh. Chem. 2002 133 199
41. Bieber L W., da Silva M F., Tetrahedron Lett. 2004 45 8281
42. Kabalka G W., Zhou L.-L, Wang L, Pagni R M., Tetrahedron 2006 62 857
43. Sharifi A, Mirzaei M, Naimi-Jamal M R., J. Chem. Res. 2007 129
44. Wang M, Li P, Wang L, Eur. J. Org. Chem. 2008 2255
45. Li P, Wang L, Tetrahedron 2007 63 5455
46. Stephens R D., Castro C E., J. Org. Chem. 1963 28 3313
47. Asano Y, Hara K, Ito H, Sawamura M, Org. Lett. 2007 9 3901
48. Asano Y, Ito H, Hara K, Sawamura M, Organometallics 2008 27 5984
49. Li C.-J, Chan T.-H, In Organic Reactions in Aqueous Media John Wiley and Sons New York 1997
50. Li C.-J, Acc. Chem. Res. 2010 43 581
51. Chen L, Li C.-J, Adv. Synth. Catal. 2006 348 1459
52. Kobayashi S, Chem. Lett. 1991 2187
53. Kobayashi S, Hachiya I, J. Org. Chem. 1994 59 3590
54. Dureen M A., Stephan D W., J. Am. Chem. Soc. 2009 131 8396