Preparation and stereoselective additions of highly substituted cyclic allylzinc reagents: A zinc-ene cyclization

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7779-7782

  Millot, Nicolas ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZONITRILE; KETONE; ZINC DERIVATIVE;

ACYLATION; ARTICLE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033615777     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01689-5     Document Type: Article

References (16)

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3. 3) a) Jones, P.; Millot, N.; Knochel, P. Chem. Commun. 1998, 2405;
4. b) Jones, P.; Knochel, P. Chem. Commun. 1998, 2407;
5. c) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186.
6. 4) a) Herrmann, J.L.; Kieczykowski, G.R., Schlessinger, R.H. Tetrahedron Lett. 1973, 26, 2433;
7. b) Rathke, M.W., Sullivan, D. Tetrahedron Lett. 1972, 41, 4249.
8. 20O: 252.1509, found: 252.1525.
9. 6) The 5-membered ring alcohol 5d was prepared in three steps from cyclopentenyl tert-butyl ketone according to Scheme 2.
10. 2, THF, -78 °C to rt, 3 h (70 % yield).
11. 8) The relative diastereoselectivity of compounds 2 was assigned according to the previously published NMR data: Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
12. 9) a) Oppolzer, W. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 5, p. 29;
13. b) Oppolzer, W.; Ando, A.; Chimia 1992, 46, 122;
14. c) Oppolzer, W.; Bienaymé, H.; Genevois-Borelle, A. J. Am. Chem. Soc. 1991, 113 , 9660;
15. d) Meyer, C.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1996, 37, 857.
16. 10) X-Ray analyses were performed by measuring intensity data on a Enraf-Nonius CAD-4 diffractometer using graphite-monochromated Cu Kα radiation and the ω scan technique up to θ = 70°. Lists of atomic coordinates, bond distances, bond angles, torsional angles have been deposited at the Cambridge Crystallographic Data Center (n° CCDC 125015).