The Mannich-type reaction between N,O-acetals and carbon nucleophiles under solvent-free conditions

Heterocycles

Volumn 67, Issue 1, 2006, Pages 113-117

  Matsumura, Yoshihiro ^a   Ikeda, Takashi ^a   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646789112     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(T)34     Document Type: Article

References (43)

1. A recent review. Speckamp W.N., and Moolenaar M.J. Tetrahedron 56 (2000) 3817
2. Some recent literatures. Veerman J.J.N., Klein J., Aben R.W.N., Scheeren H.W., Kruse C.G., Van Maarseveen J.H., Rutjes F.P.J.T., and Hiemstra H. Eur. J. Org. Chem. (2002) 3133
3. Andrews D.M., Borthwick A.D., Chaignot H., Jones P.S., Robinson J.E., Shah P., Slater M.J., and Upton R.J. Synthesis (2003) 1722
4. Albrecht U., Armbrust H., and Langer P. Synthesis 143 (2004)
5. Rudolph A.C., Machauer R., and Martin S.F. Tetrahedron Lett. 45 (2004) 4895
6. Hjelmgaard T., Sotofte I., and Tanner D. J. Org. Chem. 70 (2005) 5688
7. Shono T., Hamaguchi H., and Matsumura Y. J. Am. Chem. Soc. 97 (1975) 4264
8. Shono T., Matsumura Y., and Tsubata K. Org. Synth., Coll. Vol. VII (1990) 307
9. Wanyoike G.N., Onomura O., Maki T., and Matsumura Y. Org. Lett. 4 (2002) 1875
10. Shono T., Matsumura Y., Onomura O., Kanazawa T., and Habuka M. Chem. Lett. 1101 (1984)
11. Matsumura Y., Kanda Y., Shirai K., Onomura O., and Maki T. Org. Lett. 1 (1999) 175
12. Matsumura Y., Kanda Y., Shirai K., Onomura O., and Maki T. Tetrahedron 56 (2000) 7411
13. Onomura O., Kanda Y., Nakamura Y., Maki T., and Matsumura Y. Tetrahedron Lett. 43 (2002) 3229
14. Matsumura Y., Onomura O., Suzuki H., Furukubo S., Maki T., and Li C.-J. Tetrahedron Lett. 44 (2003) 5519
15. Oxford. Anastas P.T., and Warner C. Green Chemistry, Theory and Practice (1998)
16. Metzger J.O. Angew. Chem., Int. Ed. Engl. 37 (1998) 2975
17. Verma R.S. Green Chem. (1999) 43
18. Tanaka K., and Toda F. Chem. Rev. 100 (2000) 1025
19. Long J., Hu J., Shen X., Ji B., and Ding K. J. Am. Chem. Soc. 124 (2002) 10
20. Lee J.-C., Tai C.-A., and Hung S.-C. Tetrahedron Lett. 43 (2002) 851
21. McCluskey A., Robinson P.J., Hill T., Scott J.L., and Edwards J.K. Tetrahedron Lett. 43 (2002) 3117
22. Kwong F.Y., Lai C.W., and Chan K.S. Tetrahedron Lett. 43 (2002) 3537
23. Sharghi H., and Hosseini M. Synthesis (2002) 1057
24. Andrews P.C., Peatt A.C., and Raston C.L. Tetrahedron Lett. 45 (2004) 243
25. Zachova H., Man S., Necas M., and Potacek M. Eur. J. Org. Chem. (2005) 2548
26. Xiao D., Wang L., and Feng X. Synlett (2005) 1531
27. Zhang X., and Lu S. Synlett (2005) 1535
28. Shono T., Matsumura Y., and Tsubata K. J. Am. Chem. Soc. 103 (1981) 117
29. Louwrier S., Tuynman A., and Hiemstra H. Tetrahedron 52 (1996) 2629
30. Shono T., Matsumura Y., Uchida K., Tsubata K., and Makino A. J. Org. Chem. 49 (1984) 300
31. Shono T., Matsumura Y., Ogaki M., and Onomura O. Chem. Lett. (1987) 1447
32. Nagasaka T., Nishida S., Sugihara S., Kawahara T., Adachi K., and Hamaguchi F. Heterocycles 39 (1994) 171
33. Camilo N.S., and Pilli R.A. Tetrahedron Lett. 45 (2004) 2821
34. 4 (0.1 mmol, 0.197 mL) at room temperature. After stirring for 12 h, the reaction mixture was subjected on chromatography (silica gel, ethyl acetate: n-hexane=1:3) to afford 3ap in 89% yield.
35. 4 (0.1 equiv.) was stable.
36. 2 (entries 6 and 9) is hardly rationalized.
37. The dependency of the yields of 3ap-3r on nucleophiles (4p-r) (entries 4, 8 and 11) can be explained in terms of the high degree of enolization of 1,3-diketones and β-keto esters in comparison with malonic acid esters. Gero A. J. Org. Chem. 19 (1954) 1960
38. 3, δ) spectral data of new compounds are shown below. 3as: 1.60-2.33 (m, 4H), 2.19 (s, 3H), 2.85-3.80 (m, 2H), 3.66 and 3.69 (2s, 3H), 4.30-4.40, 5.10-5.18 and 5.58-5.62 (3m, 1H), 4.65-4.80 (m, 1H), 7.38-7.65 (m, 3H), 7.82-8.11 (m, 2H). 3at: 1.62-1.82 (m, 2H), 2.00-2.28 (m, 1H), 2.35-2.48 (m, 1H), 2.85-3.10 (m, 1H), 3.25-3.50 (m, 1H), 3.58 and 3.61 (2s, 3H), 4.58-4.82 (m, 1H), 5.78 and 6.40 (2d, J=4.0 and 4.0 Hz, 0.25H and 0.75H), 7.38-7.62 (m, 6H), 7.85-8.05 (m, 4H). 3au: 1.49-2.63 (m, 10H), 3.40-3.80 (m, 5.5H), 4.69-4.78 (m, 1H), 10.78 (br s, 0.5H). 3bp: 1.78-2.30 (m, 4H), 2.17 (br s, 6H), 3.30-3.40 (m, 1H), 3.45-3.52 (m, 1H), 4.00-4.50 (m, 1H), 4.45 (br s, 1H), 5.13 (br s, 2H), 7.36 (s, 5H). 3bt: 1.62-2.50 (m, 4H), 2.90-3.00 (m, 1H), 3.10-3.55 (m, 1H), 4.60-4.75 (m, 1H), 4.98-5.30 (m, 2H), 7.20-7.45 (m, 10H), 7.50-7.58 (m, 2H), 7.65-7.75 (m, 1H), 7.90-8.00 (m, 2H).
39. Shono T., Matsumura Y., Tsubata K., and Uchida K. J. Org. Chem. 51 (1986) 2590
40. Shono T., Matsumura Y., Onomura O., and Sato M. J. Org. Chem. 53 (1988) 4118
41. Mikami K., and Terada M. Tetrahedron 48 (1992) 5671
42. Mikami K., Motoyama Y., and Terada M. J. Am. Chem. Soc. 116 (1994) 2812
43. The ee's were determined by a chiral HPLC method: Daicel Chiralcel OJ (4.6 mmø, 25 cm), n-hexane, flow rate: 1.0 mL/min, detection at 210 nm, retention time: 10 min for (R)-(+)-isomer and 13 min for (S)-(-)-isomer.