Enantioselective synthesis via sparteineinduced asymmetric deprotonation

Pure and Applied Chemistry

Volumn 66, Issue 7, 1994, Pages 1479-1486

  Hoppe, D ^a   Hintze, F ^b   Tebben, P ^b   Paetow, M ^b   Ahrens, H ^a   Schwerdtfeger, J ^b   Sommerfeld, P ^a   Haller, J ^a   Guarnierp, W ^a   Kolczewsk, S ^a   Hense, T ^a   Hoppe, I ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344799549     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/pac199466071479     Document Type: Article

References (30)

1. a) M. Murakata, M. Nakajmi, K. Koya, J. Chenu Soc., Chem. Commun. 1657 (1990); references, b) P. J. Cox, N. S. Simpkins, Tetrahedron Asymmetry 2, 1 (1991); references.
2. Reviews: a) D. Hoppe, T. Krämer, J.-R. Schwark, O. Zschage, Pure and Appl. Chem. 62, 1999 (1990). b) H. Kunz, H. Waldmann, Chemtracts, Org. Chem. 3, All (1990).
3. a) D. Hoppe, T. Krämer, Angew. Chem. 98, 171 (1986); Angew. Chem., Int. Ed. Engl. 25, 160 (1986). b) O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 48, 8377 (1992).
4. D. Hoppe, F. Hintze, P. Tebben, Angew. Chem. 102, 1457 (1990); Angew. Chem., Int. Ed. Engl. 29, 1422 (1990). b) short review: P. Knochel, Angew. Chem. 104,1486 (1993); Angew. Chem., Int. Ed. Engl. 31, 1459 (1993).
5. F. Hintze, D. Hoppe, Synthesis 1216 (1992).
6. For the first report on the configurational stability of l-(alkoxymethoxy)alkyllithium see: W. C. Still, C. Sreekumar, J. Am. Chem. Soc. 102, 1201 (1980).
7. Review: K. Tomioka, Synthesis 541 (1990).
8. a) H. Nozaki, T. Aratani, R. Noyori, Tetrahedron 27, 905 (1971). b) H. Nozaki, T. Aratani, T. Toraya, Tetrahedron Lett. 4097 (1968).
9. M. Guetté, J. Capillon, J.-P. Guetté, Tetrahedron 29, 3659 (1973).
10. P. Beak, H. Du, J. Am. Chem. Soc. 115, 2516 (1993).
11. N. G. Rondan, K. N. Hook, P. Beak, W. J. Zajdel, J. Chandresekhar, P. v. Ragué Schleyer, J. Org. Chem. 46, 4108 (1981).
12. D. Hoppe, R. Hanko, A. Brönneke, F. Lichtenberg, Angew. Chem. 93,1106 (1981); Angew. Chem., Int. Ed. Engl. 20,1024 (1981).
13. D. Hoppe, M. Paetow, F. Hintze, Angew. Chem. 105, 430 (1993); Angew. Chem., Int. Ed. Engl. 32, 394 (1993).
14. E.-U. Würthwein, unpublished.
15. sec-Butyllithium is a chiral and racemic compound. Its replacement by isopropyllithium does not cause significant changes in stereoselectivity, see ref. R.
16. D. J. Gallagher, S. T. Kerrick, P. Beak, J. Am. Chem. Soc. 114, 5872 (1992).
17. F. Hintze, Dissertation, Univ. of Kiel, 1993.
18. I. Hoppe, unpublished.
19. J. Schwerdtfeger, D. Hoppe, Angew. Chem. 104, 1547 (1992); Angew. Chem., Int. Ed. Engl. 31; 1505 (1992).
20. P. Sommerfeld, D. Hoppe, Synlett 764 (1992).
21. M. Paetow, Dissertation, Univ. of Kiel, 1993.
22. M. Paetow, H. Ahrens, D. Hoppe, Tetrahedron Lett. 33, 5323 (1992).
23. H. Ahrens, M. Paetow, D. Hoppe, Tetrahedron Lett. 33, 5327 (1992).
24. S. T. Kerrick, P. Beak, J. Am. Chem. Soc. 113, 9708 (1991).
25. J. Haller, T. Hense, D. Hoppe, Synlett accepted.
26. Review: S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 97,1 (1985); Angew. Chem., Int. Ed. Engl. 24,1 (1985).
27. S. Kolczewski, unpublished.
28. W. Guamieri, Diploma Thesis, Univ. of Kiel, 1992.
29. I. Hoppe, D. Hoppe, manuscript in preparation.
30. G. Boche, M. Marsch, K. Harms, unpublished.