Enantioselective synthesis of α,α'-disubstituted piperidines via ruthenium-catalyzed ring rearrangement

Synthesis

Volumn , Issue 6, 2000, Pages 893-898

  Voigtmann, Ulrike ^a   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Azasugars; Dihydroxylations; Indolizidines; Metathesis; Osmiu m; Piperidines; Rearrangements; Ruthenium

Indexed keywords

PIPERIDINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034051322     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6267     Document Type: Article

References (21)

1. (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
2. (b) Schuster, M., Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
3. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371.
4. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37.
5. (a) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 166.
6. (b) Crimmins, M. T.; Choy, A. L. J. Am. Chem.Soc. 1999, 121, 5653.
7. (c) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424.
8. (d) Ziegler, F. E.; Wang, Y. J. Org. Chem. 1998, 63, 426.
9. (a) Grubbs, R. H. J. Macromol. Sci. Chem. 1994, A31, 1829.
10. (b) Schrock, R. R. Pure Appl. Chem. 1994, 66, 1447.
11. (a) Schneider, M. F.; Lucas, N., Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257.
12. (b) Schneider, M. F.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 55, 410.
13. Stragies, R.; Blechert, S. Synlett 1998, 169.
14. (a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634.
15. (b) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem 1998, 63, 8626.
16. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
17. Stragies, R.; Blechert, S. Tetrahedron 1999, 55, 8179.
18. For example Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677.
19. (a) Kaneko, C.; Sugimoto, A.; Tanaka, S. Synthesis 1974, 876.
20. (b) Johnson, C. R.; Bis, S. J., Tetrahedron Lett. 1992, 33, 7287.
21. Iminosugars as Glucosidaseinhibitors, Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1998.