Efficient synthesis of bicyclo[2.2.1]heptane derivatives via stereoselective intramolecular Michael reactions of vinyl sulfones

Tetrahedron

Volumn 52, Issue 26, 1996, Pages 8795-8806

  Collins, Mark A ^a,b   Jones, D Neville ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b WYETH AYERST RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029898998     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00421-8     Document Type: Article

References (20)

1. For a review of allyl sulfones see Haynes, R.K. 'Allyl Phenyl Sulfone' in The Encyclopedia of Reagents For Organic Synthesis, Ed. Paquette, L.A. John Wiley and Sons, Chichester, UK, Vol I, 1995.
2. For a review of vinyl sulfones see Simpkins, N.S. Tetrahedron 1990, 46, 6951.
3. Binns, M.R.; Haynes, R.K.; Katsifis, A.G.; Schober, P.A.; Vonwiller, S.C. J. Org. Chem. 1989, 54, 1961.
4. Collins, M.A.; Jones, D.N. Tetrahedron Lett. 1995, 36, 4467.
5. Jones, D.N.; Maybury, M.W.J.; Swallow, S.; Tomkinson, N.C.O. Tetrahedron Lett. 1993, 34, 8553.
6. Hirama, M. Tetrahedron Lett. 1981, 22, 1905.
7. Kraus, G.; Frazier, K. Synth. Commun. 1978, 8, 483.
8. Vasil'eva, L.L.; Mel'nikova, V.I.; Gainullina, E.T.; Pivnitskii, K.K. J. Org. Chem. USSR. 1983, 19, 835.
9. Broaddus, C.D. Acc. Chem. Res. 1968, 1, 231.
10. Haynes, R.K.; Katsifis, A.G. Aust. J. Chem. 1989, 42, 1473.
11. In our hands, mixtures of α-1,4- and, predominately, γ-1,4-addition products were usually isolated (see ref. 7). Using shorter reaction times (see ref. 4), we tended to recover significant amounts of unreacted starting material.
12. The vinyl sulfones 13 and 17 were assigned the trans configuration on the basis of the coupling constant (11Hz) between H-2 and H-3.
13. During the course of another investigation, the three component coupling of sulfone 18, 2-methylcyclopentenone, and 2-bromomethylthiophene produced the bicyclic compound 35 in 63% yield. (figure presented)
14. Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
15. Brugel, W. Nuclear Magnetic Resonance Spectra and Chemical Structure, Academic Press, New York, 1967.
16. Johnson, F. Chem. Rev. 1968, 68, 375.
17. Desulfonylation of the bicyclic ketones was complicated by side products arising as a result of the presence of the 2-keto functionality.
18. Erman, W. Chemistry Of The Monoterpenes, Part B, Marcel Dekker Inc. New York, 1985.
19. Trost, B.M.; Arndt, H.C.; Strege, P.E.; Verhoeven, T.R. Tetrahedron Lett. 1976, 17, 3477.
20. Still, W.C.; Khan, M; Mitra, A. J. Org. Chem. 1978, 43, 2923.