Synthesis of optically active 2-siloxycyclopropanecarboxylates by asymmetric catalysis, IV: Influence of nucleophilicity of silyl enol ethers on stereoselectivities in asymmetric cyclopropanation reactions

Liebigs Annales

Volumn , Issue 3, 1997, Pages 521-526

  Schumacher, Ralf ^a   Reißig, Hans Ulrich ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Asymmetric catalysis; Copper; Cyclopropanecarboxylates, 2 siloxy; Diazoacetates; Silyl enol ethers; 2+1 Cycloadditions

Indexed keywords

EID: 33748815662     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970312     Document Type: Article

References (33)

1. Part III: R. Schumacher, F. Dammast, H.-U. Reißig, Chem. Eur. J. 1997, in press.
2. R. Schumacher, Dissertation, Technische Universität Dresden, 1996.
3. [3a] H. Nozaki, S. Moriuti, H. Takaya, R. Noyori, Tetrahedron Lett. 1966, 5239-5244.
4. [3b] H. Nozaki, H. Takaya, S. Moriuti, R. Noyori, Tetrahedron 1968, 24, 3655-3669.
5. For a recent review see: H.-U. Reißig in Stereoselective Synthesis of Organic Compounds/Methods of Organic Chemistry (Houben-Weyl), 4. Ed., Vol. E 21c (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, Stuttgart, 1995, p. 3179-3270.
6. For a review considering the nucleophilicity of olefins see: H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010;
7. Angew. Chem. Int. Ed. Engl. 1994, 33, 958.
8. K. Ito, T. Katsuki, Tetrahedron Lett. 1993, 34, 2661-2664.
9. K. Ito, T. Katsuki, Synlett 1993, 638-640.
10. [8a] H. O. House, L. J. Czuba, M. Gall, H. D. Olmstead, J. Org. Chem. 1969, 34, 2324-2336.
11. [8b] Y. Tamaguchi, J. Inauaga, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1981, 54, 3229-3230.
12. [9a] T. Aratani, Y. Yoneyoshi, T. Nacase, Tetrahedron Lett. 1975, 1707-1710.
13. [9b] T. Aratani, Y. Yoneyoshi, T. Nagase, Tetrahedron Lett. ibid. 1977, 2599-2602.
14. [9c] T. Aratani, Y. Yoneyoshi, T. Nagase, Tetrahedron Lett. ibid 1982, 23, 685-688.
15. [9d] T. Aratani, Pure Appl. Chem. 1985, 57, 1839-1844.
16. [10a] T. Kunz, H.-U. Reißig, Tetrahedron Lett. 1989, 30, 2079-2082.
17. [10b] F. Dammast, H.-U. Reißig, Chem. Ber. 1993, 126 2449-2456.
18. [10c] F. Dammast, H.-U. Reißig, Chem. Ber. ibid. 1993, 726, 2727-2732.
19. [11a] D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728.
20. [11b] D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439-441;
21. Angew. Chem. Int. Ed. Engl. 1992, 31, 430.
22. R. G. Salomon, J. K. Kochi, J. Am. Chem. Soc. 1973, 95, 3300-3310.
23. [13a] E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728-729.
24. [13b] D. A. Evans, S. J. Miller, T. Lectka, J. Am. Chem. Soc. ibid. 1993, 115, 6460-6461.
25. D. A. Evans, J. A. Murry, M. C. Kozlowski, J. Am. Chem. Soc. 1996, 118, 5814-5815.
26. A detailed mechanistic discussion will be published in part V of this series, taking into account the induced absolute configuration: R. Schumacher, H.-U. Reißig, Liebigs Ann., submitted.
27. N. E. Searle, Org. Synth. Coll. Vol. IV 1963, 424-426.
28. G. Umbricht, Dissertation, Universität Basel, 1993. - In our hands, the reaction of tert-leucinol and 2,2-dimethylmalonodinitrile gave ligand 3 in 97% yield.
29. D. Seyferth, G. J. Murphy, B. Mauzé, J. Am. Chem. Soc. 1977, 99, 5317-5330.
30. C. H. Heathcock, M. H. Norman, D. E. Uehling, J. Am. Chem. Soc. 1985, 107, 2797-2799.
31. H. E. Zimmermann, S. A. Fleming, J. Org. Chem. 1985, 50, 2539-2551.
32. B. A. Gostevski, O. A. Vjasankina, H. C. Vjasankin, Zh. Obshch. Khim. 1984, 54, 2613-2617.
33. E. Kunkel, I. Reichelt, H.-U. Reißig, Liebigs Ann. Chem. 1984, 512-530.