Syntheses of tetrahydropyridin-3-ol and tetrahydroazepin-3-ol from a chiral aziridine-2-carboxylate

Tetrahedron

Volumn 63, Issue 16, 2007, Pages 3321-3327

  Lee, Hyeon Kyu ^a   Im, Jung Hee ^a   Jung, Sang Hun ^b  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Chungnam National University   (South Korea)

Author keywords

Aziridine 2 carboxylate; Tetrahydro 1H azepin 3 ol; Tetrahydropyridin 3 ol

Indexed keywords

AZEPINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ALLYLATION; ARTICLE; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33947208008     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.045     Document Type: Article

References (56)

1. Buffat M.G.P. Tetrahedron 60 (2004) 1701
2. Weintraub P.M., Sabol J.S., Kane J.M., and Borcherding D.R. Tetrahedron 59 (2003) 2953
3. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645
4. Michael J.P. Nat. Prod. Rep. 21 (2004) 625
5. Bailey P.D., Millwood P.A., and Smith P.D. Chem. Commun. (1998) 633
6. O'Hagen D. Nat. Prod. Rep. 14 (1997) 637
7. Schneider M.J. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 10 (1996), Pergamon, Oxford 155-299
8. For polyhydroxylated piperidines (azasugars), see:
9. Afarinkia K., and Bahar A. Tetrahedron: Asymmetry 16 (2005) 1239
10. Stutz A.E. Iminosugars as Glycosidase Inhibitors (1998), Wiley-VCH, Weinheim
11. Sears P., and Wong C.H. Angew. Chem., Int. Ed. 38 (1999) 2300
12. Jacob G.S. Curr. Opin. Struct. Biol. 5 (1995) 605
13. Hughes A.B., and Rudge A.J. Nat. Prod. Rep. 11 (1994) 135
14. For some representative examples of previous work in this area, see:
15. Martin R., Murruzzu C., Pericas M.A., and Riera A. J. Org. Chem. 70 (2005) 2325
16. Kato A., Kato N., Kano E., Adachi I., Ikeda K., Yu L., Okamoto T., Banba Y., Ouchi H., Takahata H., and Asano N. J. Med. Chem. 48 (2005) 2036
17. Toyooka N., and Nemoto H. Drugs Future 27 (2002) 143
18. Mehta G., and Mohal N. Tetrahedron Lett. 41 (2000) 5741
19. Sun H., Millar K.M., Yang J., Abboud K., and Horenstein B.A. Tetrahedron Lett. 41 (2000) 2801
20. Yokoyama H., Otaya K., Kobayashi H., Miyazawa M., Yamaguchi S., and Hirai Y. Org. Lett. 2 (2000) 2427
21. Davis F.A., Chao B., Fang T., and Szewczyk J.M. Org. Lett. 2 (2000) 1041
22. Toyooka N., Yoshida Y., Yotsui Y., and Momose T. J. Org. Chem. 64 (1999) 4914
23. See Ref. 1e;
24. Yoda H., Kawauchi M., and Takabe K. Synlett (1998) 137
25. Goti A., Cardona F., and Brandi A. Synlett (1996) 761
26. Altenbach H.-J., and Himmeldirk K. Tetrahedron: Asymmetry 6 (1995) 1077
27. Nukui S., Sodeoka M., Sasai H., and Shibasaki M. J. Org. Chem. 60 (1995) 398
28. Cook G.R., Beholz L.G., and Stille J.R. J. Org. Chem. 59 (1994) 3575
29. Casiraghi G., Rassu G., Spanu P., Pinna L., and Ulgheri F. J. Org. Chem. 58 (1993) 3397
30. Lee H.K., Chun J.S., and Pak C.S. J. Org. Chem. 68 (2003) 2471
31. Lee H.K., Chun J.S., and Pak C.S. Tetrahedron 59 (2003) 6445
32. Lee H.K., Chun J.S., and Pak C.S. Tetrahedron Lett. 42 (2001) 3483
33. Trost B.M., and Fandrick D.R. Org. Lett. 7 (2005) 823
34. Lee W.K., and Ha H.-J. Aldrichimica Acta 36 (2003) 57
35. Concellon J.M., Riego E., and Suarez. J. Org. Chem. 68 (2003) 9242
36. Sweeney J.B. Chem. Soc. Rev. 31 (2003) 247
37. Chandrasekhar M., Sekar G., and Singh V.K. Tetrahedron Lett. 41 (2000) 10079
38. Nayak S.K., Thijs L., and Zwanenburg B. Tetrahedron Lett. 40 (1999) 981
39. Haner R., Olano B., and Seebach D. Helv. Chim. Acta 70 (1987) 1679
40. Lee H.K., Kim E.-K., and Pak C.S. Tetrahedron Lett. 43 (2002) 9641
41. Williams L.M., and Davis J.T. Tetrahedron Lett. 39 (1998) 9135
42. Yun J.M., Sim T.B., Hahm H.S., Lee W.K., and Ha H.-J. J. Org. Chem. 68 (2003) 7675
43. Kim B.C., and Lee W.K. Tetrahedron 52 (1996) 12117
44. Choi S.K., Lee J.S., Kim J.H., and Lee W.K. J. Org. Chem. 62 (1997) 743
45. Bae J.H., Shin S.-H., Park C.S., and Lee W.K. Tetrahedron 55 (1999) 10041
46. Park S.O., Kang H.J., Ko S., Park S., and Chang S. Tetrahedron: Asymmetry 12 (2001) 2621 For recent reviews on RCM, see:
47. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18
48. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
49. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815
50. Basha A., Lipton M., and Weinreb S.M. Tetrahedron Lett. (1977) 4171
51. Lee E., Song H.Y., Kang J.W., Kim D.S., Jung C.K., and Joo J.M. J. Am. Chem. Soc. 124 (2002) 384
52. Jonghe S.D., Lamote I., Venkataraman K., Boldin S.A., Hillaert U., Rozenski J., Hendrix C., Busson R., Keukeleire D.D., Calenbergh S.V., Futerman A.H., and Herdewijn P. J. Org. Chem. 67 (2002) 988
53. Aggarwal V.K., Astle C.J., and Rogers-Evans M. Org. Lett. 6 (2004) 1469
54. Trost B.M., and Yeh V.S.C. Org. Lett. 4 (2002) 3513
55. Sletten E.M., and Liotta L.J. J. Org. Chem. 71 (2006) 1335
56. 8a