Synthesis of polycyclic polyfunctionalized carbocycles by a cobalt(I)-initiated tandem Diels - Alder reaction sequence

Israel Journal of Chemistry

Volumn 41, Issue 4, 2001, Pages 317-328

  Hilt, Gerhard ^a   Lüers, Steffen ^a   Polborn, Kurt ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013350768     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1560/8E4X-0U34-MQYD-0H20     Document Type: Article

References (21)

1. (a) Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem., Int. Ed. Engl. 2001, 40, 2004.
2. (b) Wender, P.A.; Handy, S.T.; Wright, D.L. Chem. Ind. 1997, 765.
3. (c) Poss, C.S.; Schreiber, S.L. Acc. Chem. Res. 1994, 27, 9.
4. (d) Magnuson, S.R. Tetrahedron 1995, 51, 2167.
5. (e) Tietze, L.F.; Beifuss, U. Angew. Chem., Int. Ed, Engl. 1993, 32, 131.
6. (f) Special issue, Wender, P.A. Guest Ed.; Chem. Rev. 1996, 96, 1.
7. (g) Tietze, L.F.; Haunert, F. In Stimulating Concepts in Chemistry; Shibasaki, M.; Stoddart, J.F.; Vögtle, F., Eds.; Wiley-VCH: Weinheim, 2000; pp 39-64.
8. (h) Tietze, L.F.; Modi, A. Med. Res. Rev. 2000, 20, 304.
9. (i) Tietze, L.F. Nachr. Chem., Tech. Lab. 1997, 45, 1181.
10. (j) Bunce, R.A. Tetrahedron 1995, 51, 13103.
11. Carruthers, W. In Cycloaddition Reactions in Organic Synthesis; Baldwin, J.E.; Magnus, P.D., Eds.; Pergamon Press: Oxford, 1990.
12. (a) Neuschuetz, K.; Velker, J.; Neier, R. Synthesis 1998, 227.
13. (b) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87.
14. (c) Winkler, J.D. Chem. Rev. 1996, 96, 167.
15. For a review, see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49 and references cited therein. For mechanistic considerations, see Lautens, M.; Tam, W.; Lautens, J.C.; Edwards, L.G.; Crudden, C.M.; Smith, A.C. J. Am. Chem. Soc. 1995, 117, 6863.
16. For a review, see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49 and references cited therein. For mechanistic considerations, see Lautens, M.; Tam, W.; Lautens, J.C.; Edwards, L.G.; Crudden, C.M.; Smith, A.C. J. Am. Chem. Soc. 1995, 117, 6863.
17. (a) Hilt, G.; du Mesnil, F.-X. Tetrahedron Lett. 2000, 41, 6757.
18. (b) Hilt, G.; Korn T.J. Tetrahedron Lett. 2001, 42, 2783.
19. In the absence of the catalyst, no neutral Diels - Alder reactions were observed under otherwise identical conditions for all transformations described here. The rate of the reaction was enhanced when the amount of catalyst for the neutral Diels - Alder reactions was increased with 1,3-dienes. However, for the reactions with norbornadiene, not more than 3 mol% should be used. Otherwise, the strong exothermic reaction cannot be controlled. The use of less than 1.0 mol% of catalyst is acceptable for the reactive starting materials, whereas for higher substituted starting materials, generally the reaction rate drops considerably.
20. For crystallographic data, see experimental section.
21. Thomas, A. F.; Bucher, W. Helv. Chim. Acta 1970, 53, 85.