On the faciality of intramolecular Palladium(0)-Catalysed 'metallo-ene-type' cyclisations

Tetrahedron

Volumn 53, Issue 10, 1997, Pages 3577-3586

  Oppolzer, Wolfgang ^a   Stammen, Blanda ^b  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562372     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00077-X     Document Type: Article

References (21)

1. 3. Oppolzer, W.; Gaudin, J.-M.; Bedoya-Zurita, M.; Hueso-Rodriguez, J.; Raynham, T.M.; Robyr, C. Tetrahedron Lett. 1988, 29, 4709-4712.
2. 4. Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266-1274.
3. 5. Oppolzer, W.; Schröder, F. Tetrahedron Lett. 1994, 35, 7939-7942.
4. 6. a) Oppolzer, W.; Robyr, C. Tetrahedron 1994, 50, 415-424.
5. b) Oppolzer, W.; Bienaymé, H.; Genevois-Borella, A. J. Am. Chem. Soc. 1991,113, 9660-9661.
6. 7. Reviews: a) Oppolzer, W.: Transition Metal Allyl Complexes: Intramolecular Alkene and Alkyne Insertions. In Comprehensive Organometallic Chemistry, Abel, E.W., Stone, F.G.A., Wilkinson, G. Eds.; Pergamon, Oxford 1995, vol. 12, pp. 905-921.
7. b) Oppolzer, W.: Stereocontrolled, Catalytic Transition Metal-Ene Type Cyclizations In Organic Synthesis. In Organometallic Reagents in Organic Synthesis; Bateson, J.H.; Mitchell, M. B. Eds.; Academic Press, Ltd.: London 1994; pp. 161-183.
8. c) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941-1948.
9. d) Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1989, 28, 38-52.
10. 8. Oppolzer, W.; Gaudin, J.-M.; Birkinshaw, T.N. Tetrahedron Lett. 1988, 29, 4705-4708.
11. 9. Oppolzer, W.;. Birkinshaw, T.N.; Bernadinelli, G. Tetrahedron Lett. 1990, 31, 6995-6998.
12. 10. Colonge, J.; Polaine, G. Bull. Soc. Chim. Fr. 1955, 953-955.
13. 11. a) Henry, J.R.; Marcin, L.R.; McIntosh, M.C.; Scola, G.D.; Harris Jr., G.D.; Weinreb, S.M. Tetrahedron Lett. 1989, 30, 5709-5712.
14. b) Degerbeck, F.; Fransson, B.; Grehn, L.; Ragnarsson, U. J. Chem. Soc. Perkin Trans. I 1992, 245-253.
15. 12. Prepared from phenylacetylene, 1.1 eq. n-BuLi, THF, -30°C, 30 min, then addition to para-formaldehyde in THF (83%); based on: Hatch, L.F.; Alexander, H.E. J. Am. Chem. Soc. 1950, 72, 5643-5645.
16. 1H NMR, see Scheme 3.
17. 14. a) Fleming, I.; Chan, T.H. Synthesis 1979, 761-786.
18. b) Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349-370.
19. 15. Oppolzer, W., Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266-1274.
20. 16. Miller, R.B.; Reichenbach, T. Tetrahedron Lett. 1974, 543-546.
21. 17. Zweifel, G.; On, H.P. Synthesis 1980, 803-805.