The atropo-enantioselective reduction of configurationally unstable biaryl hydroxy aldehydes - A novel approach to axially chiral biaryls

Synlett

Volumn , Issue 6, 1998, Pages 634-636

  Bringmann, Gerhard ^a   Breuning, Matthias ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001499101     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1728     Document Type: Article

References (26)

1. 14
2. Bringmann, G.; Schupp, O. S. Afr. J. Chem. 1994, 47, 83.
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4. Bringmann, G.; Hartung, T.; Göbel, L.; Schupp, O.; Ewers, C. L. J.; Schöner, B.; Zagst, R.; Peters, K.; von Schnering, H. G.; Burschka, C. Liebigs Ann. Chem. 1992, 225.
5. Bringmann, G.; Harrung, T. Angew. Chem. 1992, 104, 782;
6. Angew. Chem. Int. Ed. Engl. 1992, 31, 761.
7. Bringmann, G.; Hartung, T. Tetrahedron 1993, 49, 7891.
8. Seebach, D.; Jaeschke, G.; Gottwald, K.; Matsuda, K.; Formisano, R.; Chaplin, D. A.; Breuning, M.; Bringmann, G. Tetrahedron 1997, 53, 7539.
9. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
10. Bringmann, G.; Reuscher, H. Angew. Chem. 1989, 101, 1725;
11. Angew. Chem. Int. Ed. Engl. 1989, 28, 1672.
12. Bringmann, G.; Walter, R.; Ewers, C. L. J. Synlett 1991, 581.
13. Bringmann, G.; Holenz, J.; Weirich, R.; Rübenacker, M.; Funke, C.; Boyd, M. R.; Gulakowski, R. J.; François, G. Tetrahedron 1998, 54, 497.
14. Bringmann, G.; Pabst, T.; Busemann, S.; Peters, K.; Peters, E.-M. Tetrahedron 1998, 54, 1425.
15. Bringmann, G.; Breuning, M. Tetrahedron: Asymmetry 1998, 9, 667.
16. Bringmann, G.; Hartung, T. Liebigs Ann. Chem. 1994, 313.
17. Bringmann, G.; Schöner, B.; Peters, K.; Peters, E.-M.; von Schnering, H. G.Liebigs Ann. Chem. 1994, 439.
18. Bringmann, G.; Breuning, M.; Endress, H.; Vitt, D.; Peters, K.; Peters, E.-M. Tetrahedron, in press.
19. Bringmann, G.; Vitt, D. J. Org. Chem. 1995, 60, 7674.
20. Bringmann, G.; Vitt, D.; Kraus, J.; Breuning, M. Tetrahedron, in press.
21. R = 20 min (5a-B) and 25 min (5a-A)] to 5a-A : 5a-B = 8:92. For the analogous reduction of 4a on a preparative scale, column chromatography on silica gel (petroleum ether/ ether 1:2 → 1:8) was used instead of purification by TLC.
22. Note: Due to the Cahn-Ingold-Prelog formalism, the (stereochemically identical) atropo-enantiomers of the 'A' series are M-configurated for the compounds a, c and d, and P-configurated for b (and vice versa for the 'B' series).
23. 5 with borane gave the alcohol 5a in an enantiomeric ratio of 90 : 10 in favor for the M-enantiomer 5a-A.
24. 5 For Sa, the absolute configuration was assigned by comparison with a quantum chemically calculated CD spectrum.
25. For a non-dynamic kinetic resolution of a configurationally stable biaryl lactone, see: Bringmann, G.; Hinrichs, J. Tetrahedron: Asymmetry 1997, 8, 4121.
26. The same tendency was observed in toluene as the solvent, but with lower asymmetric inductions.