Unusual macrocyclic spirocycles from tandem metathesis reactions

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7851-7854

  Wybrow, Robert A J ^a   Johnson, Leigh A ^a   Auffray, Benoit ^a   Moran, Wesley J ^a   Adams, Harry ^a   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

Macrocycles; Ring closing metathesis; Ruthenium; Spirocycles

Indexed keywords

ALKENE; ESTER DERIVATIVE; ETHER DERIVATIVE; MACROCYCLIC COMPOUND; METAL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; TANDEM METATHESIS REACTION; X RAY CRYSTALLOGRAPHY;

EID: 0037190847     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01909-3     Document Type: Article

References (16)

1. For selected recent examples and lead references see: (a) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639; (b) Heck, M. P.; Baylon, C.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2001, 3, 1989; © Schmidt, B.; Costisella, B.; Roggenbuck, R.; Westhus, M.; Wildemann, H.; Eilbracht, P. J. Org. Chem. 2001, 66, 7658.
2. For selected recent examples and lead references see: (a) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639; (b) Heck, M. P.; Baylon, C.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2001, 3, 1989; © Schmidt, B.; Costisella, B.; Roggenbuck, R.; Westhus, M.; Wildemann, H.; Eilbracht, P. J. Org. Chem. 2001, 66, 7658.
3. For selected recent examples and lead references see: (a) Ma, S.; Ni, B. Org. Lett. 2002, 4, 639; (b) Heck, M. P.; Baylon, C.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2001, 3, 1989; © Schmidt, B.; Costisella, B.; Roggenbuck, R.; Westhus, M.; Wildemann, H.; Eilbracht, P. J. Org. Chem. 2001, 66, 7658.
4. Edwards A.S., Wybrow R.A.J., Johnstone C., Adams H., Harrity J.P.A. Chem. Commun. 2002;1542.
5. Bassindale M.J., Edwards A.S., Hamley P., Adams H., Harrity J.P.A. Chem. Commun. 2000;1035.
6. Bassindale M.J., Hamley P., Leitner A., Harrity J.P.A. Tetrahedron Lett. 40:1999;3247.
7. For an account of the mechanism and activity of Ru-based metathesis catalysts see: Sanford M.S., Love J.A., Grubbs R.H. J. Am. Chem. Soc. 2001, 123, 6543.
8. Detailed elucidation of the relative quantities and specific configurations of each olefin isomer was not performed.
9. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953.
10. For a general discussion see: Eliel E.L., Wilen S.H. Stereochemistry of Organic Compounds. 1994;618 Wiley, New York.
11. 1H NMR spectroscopy. Detailed elucidation of the relative quantities and specific configurations of each olefin isomer was not performed.
12. Crystallographic data (excluding structure factors) for the structures 10 and 14 in this paper, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 191930 and 191931, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
13. The remaining mass balance of the reaction mixture consisted of high molecular weight polymeric material which was not fully characterised. Additionally, subjecting tetraene 11 to catalyst II resulted in substantial isomerisation of the allyl ether moieties to the corresponding vinyl ethers. For a recent example of olefin isomerisation mediated by II, see: Bassindale, M. J.; Hamley, P.; Harrity, J. P. A. Tetrahedron Lett. 2001, 42, 9055 and references cited therein.
14. For a similar class of rearrangement reactions see: Adams J.A., Ford J.G., Stamatos P.J., Hoveyda A.H. J. Am. Chem. Soc. 64:1999;9690.
15. Indeed, the example outlined in Scheme 1 represents a case where exclusive 5-membered ring forming RCM takes place at the expense of potentially competing 7-membered ring formation. See Ref. 2c for a discussion.
16. Bhar S., Chauhuri S.K., Sahu S.G., Panja C. Tetrahedron. 57:2001;9011.