An efficient stereoselective synthesis of (2S,3S)-3-hydroxypipecolic acid using chlorosulfonyl isocyanate

Tetrahedron Letters

Volumn 47, Issue 41, 2006, Pages 7289-7293

  Kim, In Su ^a   Ji, Yun Jung ^a   Jung, Young Hoon ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

3 Hydroxypipecolic acid; Amination; Chlorosulfonyl isocyanate; Diastereoselectivity

Indexed keywords

2 HYDROXYMETHYLPIPERIDIN 3 OL; 3 HYDROXYPIPECOLIC ACID; ANISALDEHYDE; CHLOROSULFONYL ISOCYANATE; ISOCYANATE; PHENYL GROUP; PIPECOLIC ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; AMINATION; ARTICLE; CHIRALITY; OXIDATION; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33748296374     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.040     Document Type: Article

References (49)

1. Schneider M.J. Pyridine and Piperidine Alkaloids: Chemistry and Pharmacology. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 10 (1996), Pergamon, Oxford 155-299
2. Fodor G.B., and Colasanti B. The Pyridine and Piperidine Alkaloids: Chemistry and Pharmacology. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 3 (1985), Wiley-Interscience, New York 1-90
3. Pinder A.R. Nat. Prod. Rep. 6 (1989) 67
4. Pinder A.R. Nat. Prod. Rep. 9 (1992) 17
5. Pinder A.R. Nat. Prod. Rep. 9 (1992) 491
6. Nadin A. Contemp. Org. Synth. 4 (1997) 387
7. Bailey P.D., Millwood P.A., and Smith P.D. J. Chem. Soc., Chem. Commun. (1998) 633
8. Bols M. Acc. Chem. Res. 31 (1998) 1
9. Mitchison A., and Nsdin A. J. Chem. Soc., Perkin Trans. 1 (1999) 2553
10. For recent references on the syntheses of 3-hydroxypipecolic acid, see:. Liang N., and Datta A. J. Org. Chem. 70 (2005) 10182
11. Kumar P., and Bodas M.S. J. Org. Chem. 70 (2005) 360
12. Bodas M.S., and Kumar P. Tetrahedron Lett. 45 (2004) 8461
13. Koulocheri S.D., Magiatis P., Skaltsounis A.-L., and Haroutounian S.A. Tetrahedron 58 (2002) 6665
14. Haddad M., and Larcheveque M. Tetrahedron Lett. 42 (2001) 5223
15. For recent references on the syntheses of 2-hydroxymethylpiperidin-3-ol, see:. Takahata H., Banda Y., Sasatani M., Nemoto H., Kato A., and Adachi I. Tetrahedron 60 (2004) 8199
16. Takahata H., Banda Y., Ouchi H., Nemoto H., Kato A., and Adachi I. J. Org. Chem. 68 (2003) 3603
17. Haukaas M.H., and O'Doherty G.A. Org. Lett. 3 (2001) 401
18. For recent references on the syntheses of febrifugine and/or isofebrifugine, see:. Ashoorzadeh A., and Caprio V. Synlett (2005) 346
19. Katoh M., Matsune R., Nagase H., and Honda T. Tetrahedron Lett. 45 (2004) 6221
20. Huang P.-Q., Wei B.-G., and Ruan Y.-P. Synlett (2003) 1663
21. Sugiura M., Hagio H., Hirabayashi R., and Kobayashi S. J. Am. Chem. Soc. 123 (2001) 12510
22. Sugiura M., Hagio H., Hirabayashi R., and Kobayashi S. J. Org. Chem. 66 (2001) 809
23. Sugiura M., and Kobayashi S. Org. Lett. 3 (2001) 477
24. Ooi H., Urushibara A., Esumi T., Iwabuchi Y., and Hatakeyama S. Org. Lett. 3 (2001) 953
25. Takeuchi T., Azuma K., Takakura K., Abe H., Kim H.-S., Wataya Y., and Harayama T. Tetrahedron 57 (2001) 1213
26. Takeuchi T., and Ogasawara K. Org. Lett. 2 (2000) 3193
27. Okitsu O., Suzuki R., and Kobayashi S. Synlett (2000) 989
28. For recent references on the syntheses of prosophylline and/or deoxoprosophylline, see:. Lee H.K., Chun J.S., and Pak C.S. Tetrahedron 59 (2003) 6445
29. Cossy J., Willis C., Bellosta V., and BouzBouz S. J. Org. Chem. 67 (2002) 1982
30. Koulocheri S.D., Magiatis P., and Haroutounian S.A. J. Org. Chem. 66 (2001) 7915
31. Datta A., Kumar J.S.R., and Roy S. Tetrahedron 57 (2001) 1169
32. Kim, I. S.; Zee, O. P.; Jung, Y. H. Org. Lett. 2006, 8, in press.
33. Kim, I. S.; Kim, J. D.; Ryu, C. B.; Zee, O. P.; Jung, Y. H. Tetrahedron 2006, 62, in press.
34. Kim J.D., Kim I.S., Jin C.H., Zee O.P., and Jung Y.H. Org. Lett. 7 (2005) 4025
35. Kim J.D., Kim I.S., Hua J.C., Zee O.P., and Jung Y.H. Tetrahedron Lett. 46 (2005) 1079
36. Kim J.D., Zee O.P., and Jung Y.H. J. Org. Chem. 68 (2003) 3721
37. Kim J.D., Han G., Jeong L.S., Park H.-J., Zee O.P., and Jung Y.H. Tetrahedron 58 (2002) 4395
38. Kim J.D., Lee M.H., Han G., Park H., Zee O.P., and Jung Y.H. Tetrahedron 57 (2001) 8257
39. Kim J.D., Lee M.H., Lee M.J., and Jung Y.H. Tetrahedron Lett. 41 (2000) 5073
40. Allred E.L., and Winstein S. J. Am. Chem. Soc. 89 (1967) 3991
41. Allred E.L., and Winstein S. J. Am. Chem. Soc. 89 (1967) 3998
42. Krow G.R., Yuan J., Lin G., and Sonnet P.E. Org. Lett. 4 (2002) 1259
43. Roberts D.D. J. Org. Chem. 62 (1997) 1857
44. Carlsen P.H.J., Katsuki T., Martin V.S., and Sharpless K.A. J. Org. Chem. 46 (1981) 3936
45. Nunez M.T., and Martin V.S. J. Org. Chem. 55 (1990) 1928
46. Schuda P.F., Cichowicz M.B., and Heiman M.R. Tetrahedron Lett. 24 (1983) 3829
47. Chaudhuri S.R., and Gurjar M.K. Tetrahedron Lett. 43 (2002) 2435
48. +] 146.0817, found 146.0817.
49. +] 132.1024, found 132.1024.