Asymmetric synthesis of α-alkylproline derivatives from a chiral borane-amine adduct: Inversion of enantioselectivity in the presence of a crown ether

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7244-7245

  Ferey, Vincent ^a   Vedrenne, Patrick ^a   Toupet, Loïc ^b   Le Gall, Thierry ^a   Mioskowski, Charles ^a,c  

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029907051     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961432o     Document Type: Article

References (24)

1. (1)(a) Thairivongs, S.; Pals, D. T.; Lawson, J. A.; Turner, S. R.; Harris, D. W. J. Med. Chem. 1987, 30, 536.
2. (b) Ward, P.; Ewan, G. B.; Jordan, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848.
3. Selected references: (a) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. Ibid. 1991, 34, 1777. (b) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778.
4. Selected references: (a) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. Ibid. 1991, 34, 1777. (b) Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778.
5. (a) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704.
6. (b) Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
7. (c) Bajgrowicz, J.; El Achquar, A.; Roumestant, M.-L.; Pigière, C.; Viallefont, P. Heterocycles 1986, 24, 2165.
8. (d) Schöllkopf, U.; Hinrichs, R.; Lonsky, R. Angew. Chem. 1987, 99, 137; Angew. Chem., Int. Ed. Engl. 1987, 26, 143.
9. (d) Schöllkopf, U.; Hinrichs, R.; Lonsky, R. Angew. Chem. 1987, 99, 137; Angew. Chem., Int. Ed. Engl. 1987, 26, 143.
10. (e) Shatzmiller, S.; Dolithsky, B.-Z.; Bahar, E. Liebigs Ann. Chem. 1991, 375.
11. (f) Beck, A. K.; Blank, S.; Job, K.; Seebach, D.; Sommerfeld, Th. Org. Synth. 1993, 72, 62.
12. (g) Genin, M. J.; Baures, P. W.; Johnson, R. L. Tetrahedron Lett. 1994, 35, 4967.
13. For the enantioselective synthesis of α-alkylalanine derivatives (having an unremovable N-methyl group) using such a strategy, see: Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem. 1996, 108, 475; Angew. Chem., Int. Ed. Engl. 1996, 35, 430.
14. For the enantioselective synthesis of α-alkylalanine derivatives (having an unremovable N-methyl group) using such a strategy, see: Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem. 1996, 108, 475; Angew. Chem., Int. Ed. Engl. 1996, 35, 430.
15. 3) in the same manner.
16. Atomic coordinates for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK.
17. 3.
18. (a) Wakabayashi, T.; Kato, Y. Tetrahedron Lett. 1977, 1235.
19. (b) Akabori, S.; Yoshii, T. Ibid. 1978, 4523.
20. (c) Reitsøen, B.; Kilaas, L.; Anthonsen, T. Acta Chem. Scand. 1986, B 40, 440.
21. For a recent review on the applications of crown ethers to organic synthesis, see: Lukyanenko, N. Janssen Chim. Acta 1991, 9, 3; 1992, 10, 12.
22. For a recent review on the applications of crown ethers to organic synthesis, see: Lukyanenko, N. Janssen Chim. Acta 1991, 9, 3; 1992, 10, 12.
23. A complex between a potassium enolate and a chiral crown ether has been invoked as key intermediate in an enantioselective Michael addition: Cram, D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625.
24. Beard, C. D.; Baum, K.; Grakauskas, V. J. Org. Chem. 1973, 38, 3673.