Highly Efficient Ytterbium Triflate Catalyzed Michael Additions of α-Nitroesters in Water

Synlett

Volumn 1997, Issue 7, 1997, Pages 842-844

  Keller, Erik ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542534699     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5761     Document Type: Article

References (20)

1. For recent reviews see: Li, C.-J. Chem. Rev. 1993, 93, 2023; Chan, T.H., Li, C.-J. Can. J. Chem. 1994, 72, 1181; Lubineau, A., Augé, J., Queneau, Y. Synthesis 1994, 741.
2. For recent reviews see: Li, C.-J. Chem. Rev. 1993, 93, 2023; Chan, T.H., Li, C.-J. Can. J. Chem. 1994, 72, 1181; Lubineau, A., Augé, J., Queneau, Y. Synthesis 1994, 741.
3. For recent reviews see: Li, C.-J. Chem. Rev. 1993, 93, 2023; Chan, T.H., Li, C.-J. Can. J. Chem. 1994, 72, 1181; Lubineau, A., Augé, J., Queneau, Y. Synthesis 1994, 741.
4. Cornils, B., Wiebus, E. Recl. Trav. Chim. Pays Bas 1996, 115, 211.
5. For a review see: Engberts, J.B.N.F., Feringa, B.L., Keller, E., Otto, S. Recl. Trav. Chim. Pays Bas 1996, 115, 457.
6. Kobayashi, S. Synlett 1994, 689.
7. Shipchandler, M.T. Synthesis 1979, 666.
8. Osugi, K. J. Pharm. Soc. Jpn. 1957, 77, 630.
9. Coda, A.C., Desimoni, G., Invernizzi, A.G., Righetti, P.P., Seneci, P.F., Tacconi, G. Gazz. Chim. Ital. 1985, 115, 111.
10. Feringa, B.L., de Vries, A.H.M. in Carbon-Carbon Bond Formation by Catalytic Enantioselective Conjugate Addition Chapter in Advances in Catalytic Processes JAI Press Inc. 1995, Vol. 1, 151.
11. Feringa, B.L., Jansen, J.F.G.A. In Houben-Weyl, 4th. Ed., Vol. E21, Chapter 1.5.2.4. Thieme, Stuttgart, 1995; p 2104; Jansen, J.F.G.A., Feringa, B.L. J. Org. Chem. 1990, 55, 4168; de Vries, A.H.M., Feringa, B.L. Tetrahedron 1994, 50, 4479; de Vries A.H.M., Feringa, B.L. Angew. Chem., Int. Ed. Engl. 1996, 35, 2374.
12. Feringa, B.L., Jansen, J.F.G.A. In Houben-Weyl, 4th. Ed., Vol. E21, Chapter 1.5.2.4. Thieme, Stuttgart, 1995; p 2104; Jansen, J.F.G.A., Feringa, B.L. J. Org. Chem. 1990, 55, 4168; de Vries, A.H.M., Feringa, B.L. Tetrahedron 1994, 50, 4479; de Vries A.H.M., Feringa, B.L. Angew. Chem., Int. Ed. Engl. 1996, 35, 2374.
13. Feringa, B.L., Jansen, J.F.G.A. In Houben-Weyl, 4th. Ed., Vol. E21, Chapter 1.5.2.4. Thieme, Stuttgart, 1995; p 2104; Jansen, J.F.G.A., Feringa, B.L. J. Org. Chem. 1990, 55, 4168; de Vries, A.H.M., Feringa, B.L. Tetrahedron 1994, 50, 4479; de Vries A.H.M., Feringa, B.L. Angew. Chem., Int. Ed. Engl. 1996, 35, 2374.
14. Feringa, B.L., Jansen, J.F.G.A. In Houben-Weyl, 4th. Ed., Vol. E21, Chapter 1.5.2.4. Thieme, Stuttgart, 1995; p 2104; Jansen, J.F.G.A., Feringa, B.L. J. Org. Chem. 1990, 55, 4168; de Vries, A.H.M., Feringa, B.L. Tetrahedron 1994, 50, 4479; de Vries A.H.M., Feringa, B.L. Angew. Chem., Int. Ed. Engl. 1996, 35, 2374.
15. Keller, E., Feringa, B.L. Tetrahedron Lett. 1996, 37, 1879.
16. 2, ethyl acetate:hexane = 1:9). All spectroscopic and analytic data are in accordance with the proposed structures.
17. Zen, S., Koyama, M., Koto, S. Org. Synth. 1976, 55, 77.
18. Kornblum, N., Blackwood, R.K., Powers, J.W. J. Am. Chem. Soc. 1957, 79, 2507.
19. This side reaction was not observed for the other Michael acceptors used.
20. ++1].