Ytterbium triflate catalyzed Michael additions of β-ketoesters in water

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1879-1882

  Keller, Erik ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; OXOACID;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029932703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00141-4     Document Type: Article

References (14)

1. For recent reviews see: Li, C.-J. Chem. Rev. 1993, 93, 2023; Chan, T.H., Li, C.-J., Wei, Z.Y. 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., Wei, Z.Y. 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., Wei, Z.Y. Can. J. Chem. 1994, 72, 1181; Lubineau, A., Augé, J., Queneau, Y. Synthesis 1994, 741.
4. Kobayashi, S. Synlett 1994, 689.
5. Eder, U., Sauer, G., Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496; Perlmutter P. in Conjugate Addition Reactions in Organic Synthesis, Pergamon Press Ltd., Oxford, 1992, 35, 84.
6. Eder, U., Sauer, G., Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496; Perlmutter P. in Conjugate Addition Reactions in Organic Synthesis, Pergamon Press Ltd., Oxford, 1992, 35, 84.
7. 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.
8. Feringa, B.L., Jansen, J.F.G.A. in Houben-Weyl, Volume E-21, 4th. Ed., Chapter 1.5.2.4. Thieme Verlag, Stuttgart 1995, 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.
9. Feringa, B.L., Jansen, J.F.G.A. in Houben-Weyl, Volume E-21, 4th. Ed., Chapter 1.5.2.4. Thieme Verlag, Stuttgart 1995, 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.
10. Feringa, B.L., Jansen, J.F.G.A. in Houben-Weyl, Volume E-21, 4th. Ed., Chapter 1.5.2.4. Thieme Verlag, Stuttgart 1995, 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.
11. See for example: Nelson, J.H., Howells, P.N., DeLullo, G.C., Landen, G.L. J. Org. Chem. 1980, 45, 1246; Bonadies, F., Lattanzi, A., Orelli, L.R., Pesci, S. Scretti, A. Tetrahedron Lett. 1993, 34, 7649.
12. See for example: Nelson, J.H., Howells, P.N., DeLullo, G.C., Landen, G.L. J. Org. Chem. 1980, 45, 1246; Bonadies, F., Lattanzi, A., Orelli, L.R., Pesci, S. Scretti, A. Tetrahedron Lett. 1993, 34, 7649.
13. 2, ethyl acetate: hexane =1:9). All compounds gave satisfactory spectroscopic and analytical data or data were in full agreement with these of known products. It should be noted that the aqueous catalyst solution could be reused without loss of catalytic activity.
14. House, H.O. in Modern Synthetic Reactions 2nd. ed., Benjamin Inc., Philippines 1972, 595-623.