Enantioselective Mukaiyama-Michael reactions of 2-carbomethoxy cyclopentenone catalyzed by chiral bis(oxazoline)-Cu(II) complexes

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8921-8924

  Bernardi, Anna ^a   Colombo, Giorgio ^a   Scolastico, Carlo ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANONE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030566793     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02048-5     Document Type: Article

References (23)

1. 1. Oare, D.A.; Heathcock, C.H. Topics in Stereochem. 1991, 20, 87.
2. 2. a) Kobayashi, S.; Yamada, M.; Mukaiyama, T. Chem.Lett. 1994, 97;
3. b) Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363;
4. c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. manuscript in preparation.
5. 3. Leading references on the use of these complexes in asymmetric synthesis: a) Evans, D.A.; Miller, S.J.; Lectka, T. J Am.Chem.Soc. 1993, 115, 6460;
6. b) Evans, D.A.; Murry, J.A.; von Matt, P.; Norcross, R.; Miller, S.J. Angew.Chem.Int.Ed.Engl. 1995, 34, 798.
7. c) Corey, E.J.; Imai, N.; Zhang, H.-Y. J Am.Chem.Soc. 1991, 113, 728;
8. d) Corey, E.J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807;
9. e) Johannsen, M.; Joergensen, K.A. J.Org.Chem. 1995, 60, 5757;
10. f) Gothelf, K.V.; Hazell, R.G.; Joergensen, K.A. J.Org.Chem. 1996, 61, 346;
11. g) Pfaltz, A. Acc.Chem.Res. 1993, 26, 339;
12. h) Bolm, C. Angew.Chem., Int.Ed.Engl. 1991, 30, 542;
13. i) Evans, D.A.; Faul, M.M., Bilodeau, M.T.; Anderson, B.A.; Barnes, D.M. J.Am.Chem.Soc. 1993, 115, 5328;
14. j) Helmchen, G.; Krotz, A.; Ganz, K.-T.; Hansen, D. Synlett. 1991, 257;
15. k) von Matt, P.; Pfaltz, A. Angew.Chem., Int.Ed.Engl. 1993, 32, 566;
16. 1) Evans, D.A.; Murry, J.A.; Kozlowski, M.C. J.Am.Chem.Soc. 1996, 118, 5814.
17. 4. Throughout this paper 1 was used as a ≥ 9:1 E:Z mixture.
18. 5. Lowenthal, R.E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta. 1991, 74, 232.
19. 5. Lowenthal, R.E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005; Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta. 1991, 74, 232.
20. 6 may arise from a different coordination geometry around the metal ion.
21. 7. Addition of 1 to 2 in the presence of 1 mol equiv of TBDMSOTf occurs in 2h at -78°C, to yield a mixture of 4 and 7.
22. 2 and did not behave as an effective promoter.
23. 9. For a discussion of silyltriflate catalyzed Mukaiyama reactions see: Hollis, K.T.; Bosnich, B. J.Am.Chem.Soc. 1995, 117, 4570.