Catalytic enantioselective carbon-carbon bond formation by addition of dialkyizinc reagents to cyclic 1,3-diene monoepoxides

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7795-7798

  Badalassi, Fabrizio ^a   Crotti, Paolo ^a   Macchia, Franco ^a   Pineschi, Mauro ^a   Arnold, Alexander ^b   Feringa, Ben L ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIENE MONOEPOXIDE; EPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032532776     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01704-3     Document Type: Article

References (20)

1. (1) Catalytic Asymmetric Synthesis ; Ojima, I., Ed.; VCH Publishers: New York, 1993.
2. (2) Paterson, I.; Berrisford, D.J. Angew. Chem. Int. Ed. Engl. 1992, 31, 1179.
3. (3) For leading references see: (a) Martinez, L.E.; Leighton, J.L.; Carsten, D.H.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5897.
4. (b) Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. Science 1997, 277, 936.
5. (c) Cole, B.M.; Shimizu K.D.; Kruger, C.A.; Harrity, J.P.A.; Snapper, M.; Hoveyda, A.H. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668.
6. (d) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783.
7. (e) Hodgson, D.M.; Gibbs, A.R.; Lee, G.L. Tetrahedron 1996, 52, 14361.
8. (4) (a) Davies, S.G.; Wollowitz, S. Tetrahedron Lett. 1980, 21, 4175.
9. (b) Mizuno, M.; Kanai, M.; Iida, A.; Tomioka, K. Tetrahedron: Asymmetry 1996, 7, 2483.
10. (c) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Gazz. Chim. Ital. 1997, 127, 273.
11. (5) Marshall, J.A. Chem. Rev. 1989, 89, 1503.
12. (6) Marino, J.P.; Fernandez de la Pradilla, R.; Laborde, E. J. Org. Chem. 1987, 52, 4898 and references therein.
13. (7) Lipshutz, B.H.; Woo, K.; Gross, T.; Buzard, D.J.; Tirado, R. Synlett, 1997, 47, 7.
14. (8) Berrisford, D.J.; Bolm, C.; Sharpless, K.B. Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
15. (9) (a) de Vries, A.H.M.; Meetsma, A.; Feringa, B.L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374.
16. (b) Feringa, B.L.; Pineschi, M.; Arnold, L.A.; Imbos, R.; de Vries, A.H.M. Angew. Chem. Int. Ed. Engl. 1997, 36, 2620. For a brief review, see: Krause, N. Angew. Chem. Int. Ed. Engl. 1998, 37, 283.
17. (b) Feringa, B.L.; Pineschi, M.; Arnold, L.A.; Imbos, R.; de Vries, A.H.M. Angew. Chem. Int. Ed. Engl. 1997, 36, 2620. For a brief review, see: Krause, N. Angew. Chem. Int. Ed. Engl. 1998, 37, 283.
18. 2).
19. (11) Throughout this work the ee values of the unreacted vinyloxiranes were not determined. For a discussion of kinetic resolution see Kagan, H.B.; Fiaud, J.C. Top. Stereochem. 1988, 18, 249.
20. (12) Marino, J.P.; Floyd, D.M. Tetrahedron Lett. 1979, 20, 675.