Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate

Tetrahedron Asymmetry

Volumn 17, Issue 15, 2006, Pages 2183-2186

  Garrido, Narciso M ^a   Díez, David ^a   Domínguez, Sara H ^a   García, Mercedes ^a   Sánchez, M Rosa ^a   Davies, Stephen G ^b  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE; CYCLOHEXENE DERIVATIVE; ESTER; LITHIUM; NITRO DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DECARBOXYLATION; DIASTEREOISOMER; ELIMINATION REACTION; HYDROLYSIS; PRIORITY JOURNAL;

EID: 33748688801     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.06.048     Document Type: Article

References (36)

1. Parker K.A., and Fokas D. J. Org. Chem. 71 (2006) 449-455
2. Zezula J., and Hudlicky Y. Synlett 3 (2005) 388-405
3. Hsin L.W., Chang L.T., Chen C.W., Hsu C.H., and Chen H.W. Tetrahedron 61 (2005) 513-520
4. Comins D.L., Brooks Cl.A., Al-awar R.S., and Goehring R.R. Org. Lett. 1 (1999) 229-232
5. Tori M., Shimoji T., Shimura E., Takaoka S., Nakashima K., Sono M., and Ayer W.A. Phytochemistry 53 (2000) 503-509 and references cited therein
6. Spande T.F., Jain P., Garraffo H.M., Pannell L.K., Yeh H.J.C., Daly J.W., Fukimoto S., Imara K., Tokuyama T., Torres J.A., Snelling R.R., and Jones T.H. J. Nat. Prod. 62 (1999) 5
7. Michael J.P. Nat. Prod. Rep. 15 (1998) 595
8. Toyota M., Asoh T., and Fukumoto K. Tetrahedron Lett. 37 (1996) 4401-4404
9. Back T.G., and Nakajima K. Tetrahedron Lett. 38 (1997) 989-992
10. Dijk E.W., Panella L., Pinho P., Naasz R., Meetsma A., Minnaard A.J., and Feringa B.L. Tetrahedron 60 (2004) 9687-9693
11. Davies S.G., and Bhalay G. Tetrahedron: Asymmetry 7 (1996) 1595-1596
12. Weymann M., Schultz-Kukula M., and Kunz H. Tetrahedron Lett. 39 (1997) 7835-7838
13. Oppolzer W., Flaskamp E., and Bieber L.W. Helv. Chim. Acta 84 (2001) 141-145
14. Back T.G., and Nakajima K. J. Org. Chem. 63 (1998) 6566
15. Riechers T., Krebs H.C., Wartchow R., and Habermehl G. Eur. J. Org. Chem. (1998) 2641
16. Toyota M., Asoh T., and Fukumoto K. Heterocycles 45 (1997) 147 and references cited therein
17. Urones J.G., Garrido N.M., Díez D., Domínguez S.H., and Davies S.G. Tetrahedron: Asymmetry 10 (1999) 1637-1641
18. Davies S.G., Díez D., Domínguez S.H., Garrido N.M., Kruchinin D., Price P.D., and Smith D. Org. Biomol. Chem. 3 (2005) 1284-1301
19. Tietze L.F. Chem. Rev. 96 (1996) 115-136
20. Urones J.G., Garrido N.M., Díez D., El Hammouni M.M., Domínguez S.H., Casaseca J.A., Davies S.G., and Smith D. Org. Biomol. Chem. 2 (2004) 364-372
21. Urones J.G., Garrido N.M., Díez D., Domínguez S.H., and Davies S.G. Tetrahedron: Asymmetry 8 (1997) 2683-2685
22. 1H NMR (400 MHz) spectroscopy including two-dimensional homonuclear COSY, heteronuclear HMQC and HMBC, NOE and ROESY experiments for (1R,2R,6R)-6 and (1S,2S,6S,αS)-15 are in accordance with the structure and stereochemistry assigned.
23. Aitken R.A., and Armstrong D.P. Arkivoc Vol. 1 (2000) 186-192
24. Rogic M.M., Demmin T.R., Fuhrmann R., and Koff F.W. J. Am. Chem. Soc. 97 (1975) 3241
25. To the best of our knowledge, this is the first example in which this chiral auxiliary is debenzylated to produce the nitro oxidation state.
26. Haines A.H. Methods for the oxidation of Organic Chemistry (1988), Academic Press, New York pp 220-231, 416-419
27. Kirchhoff R. Tetrahedron Lett. 29 (1976) 2533-2534
28. Ballini R., and Petrini M. Tetrahedron 60 (2004) 1017-1047 and references cited therein
29. Davies S.G., Smethurst C.A.P., Smith A.D., and Smyth G.D. Tetrahedron: Asymmetry 11 (2000) 2437-2441
30. Davies S.G., and Smyth G.D. Tetrahedron: Asymmetry 7 (1996) 1001
31. Barton D.H.R., Crich D., and Motherwell W.B. J. Chem Soc., Chem. Commun. (1983) 939
32. Barton D.H.R., and Zard S.Z. Pure Appl. Chem. 58 (1986) 675
33. Anaya J., Barton D.H.R., Caballero M.C., Gero S.D., Grande M., Laso N.M., and Hernando J.I.M. Tetrahedron: Asymmetry 5 (1994) 2137-2140
34. Barton D.H.R., Crich D., and Motherwell W.B. Tetrahedron 41 (1985) 3901
35. Motherwell W.B., and Crich D. Free Radical Chain Reactions in Organic Synthesis (1991), Academic Press
36. 3N/DCM; (v) DBU/THF/Δ.