Carbocyclisation of zinc enolates onto unactivated double bonds: A mechanistic point of view

Comptes Rendus Chimie

Volumn 6, Issue 1, 2003, Pages 67-78

  Sliwinski, Éric ^a   Prian, Fabrice ^a   Denes, Fabrice ^a   Chemla, Fabrice ^a   Normant, Jean François ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Carbocyclisation; Carbometalation; Cyclopentanes; Enolates; Piperidines; Pyrrolidines; Reformatsky reagents

Indexed keywords

CARBOXYLIC ACID; CYCLOPENTANE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0038245327     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1631-0748(03)00017-1     Document Type: Article

References (37)

1. Lorthiois E. Marek I. Normant J.-F. Tetrahedron Lett. 38 89 1997
2. Lorthiois E. Marek I. Normant J.-F. J. Org. Chem. 63 1998 566
3. Lorthiois E. Marek I. Normant J.-F. J. Org. Chem. 63 1998 2442
4. Denes F. Chemla F. Normant J.-F. Synlett 919 2002
5. Denes F. Chemla F. Normant J.-F. Eur. J. Org. Chem. 2002 3536
6. Karoyan P. Chassaing G. Tetrahedron Lett. 38 85 1997
7. Karoyan P. Triolo A. Nannicini R. Giannotti D. Altamura M. Chassaing G. Perotta E. Tetrahedron Lett. 40 71 1999
8. Chassaing G. Karoyan P. Tetrahedron: Asymm. 8 1997 2025
9. Karoyan P. Chassaing G. Tetrahedron Lett. 43 2002 253
10. Knochel P. in: Trost B Fleming I (Eds.), Comprehensive Organic Synthesis vol. 4 1991 865 Pergamon Press New York
11. Marek I. Normant J.-F. in: Diederich D Stang P (Eds.), Cross Coupling Reactions, VCH 1997 271
12. Rodriguez A.L. Bunlakananusorn T. Knochel P. Org. Lett. 2 2000 3285
13. Rosenblum M. Rosan A. Tancrede J. J. Am. Chem. Soc. 95 1973 3062
14. Lennon P. Rosan A.M. Rosenblum M. J. Am. Chem. Soc. 99 1977 8426
15. Rosenblum M. Acc. Chem. Res. 122 1974
16. Roberts B. Wong J. J. Chem. Soc., Chem. Commun. 20 1977
17. Chuang L.W. Fu H.W. Sheu B.A. Tau S.I. Yeh M.C. J. Am. Chem. Soc. 115 1993 5941
18. Lai M.L. Chang S.C. Hwu C.C. Yeh M.C. Tetrahedron Lett. 37 1996 6149
19. Yeh M.C.P. Chuang L.W. Ueng C.H. J. Org. Chem. 61 1996 3874
20. Khan Md.N.I. Pearson A.J. J. Am. Chem. Soc. 106 1984 1872
21. Clardy J.C. Cun-heng H. Khan Md.N.I. Pearson A.J. J. Am. Chem. Soc. 107 1985 2748
22. Khan Md.N.I. Pearson A.J. Tetrahedron Lett. 26 1985 1407
23. Poli G. Giambastiani G. Heumann A. Tetrahedron 56 2000 5959 and references therein
24. Balme G. Bouyssi D. Monteiro N. in: Negishi E.I. (Ed.), Handbook of Organopalladium Chemistry for Organic Synthesis 2002 2245 Wiley Interscience
25. Kitagawa O. Suzuki T. Fujiwara H. Taguchi T. Tetrahedron Lett. 40 1999 2549
26. Kitagawa O. Fujiwara H. Suzuki T. Taguchi T. Shiro M. J. Org. Chem. 65 2000 6819
27. Nakamura E. Kubota K. Tetrahedron Lett. 38 1997 7099
28. Kubota K. Nakamura E. Angew. Chem. Int. Ed. Engl. 36 1997 2491
29. Kubota K. Nakamura E. J. Org. Chem. 62 1997 792
30. Nakamura E. Sakata G. Kubota K. Tetrahedron Lett. 391 1998 2157
31. Van der Steen F.H. Kleijn H. Britovsek G.J.P. Jastrzebski J.T.B.H. Van Koten G. J. Org. Chem. 57 1992 3906
32. Orsini F. Pelizzoni F. Ricca G. Tetrahedron Lett. 25 1982 3945
33. Boersma J. Dekker J. Van der Kerk G.J.M. J. Chem. Soc., Chem. Commun. 553 1983
34. Boersma J. Budzelaar P.H.M. Dekker J. Van der Kerk G.J.M. Organometallics 3 1984 1403
35. Orsini F. Pelizzoni F. Ricca G. Tetrahedron 40 1984 2781
36. E. Lorthiois, PhD thesis, University Pierre-et-Marie-Curie (Paris-6), France, 1998
37. Prian, F. Mém. DEA, University Pierre-et-Marie-Curie (Paris-6), France