A new functionalized, chiral disulfide derived from L-cysteine: (R,R)- bis[(3-benzyloxazolan-4-yl)-methane] disulfide as a catalyst in the diethylzinc addition to aldehydes

Tetrahedron Asymmetry

Volumn 10, Issue 9, 1999, Pages 1733-1738

  Braga, Antonio L ^a   Appelt, Helmoz R ^a   Schneider, Paulo H ^a   Silveira, Claudio C ^a   Wessjohann, Ludger A ^b,c  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b UNIVERSITY OF MUNICH   (Germany)

^c VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; DISULFIDE; METHANE; ZINC;

ALCOHOL METABOLISM; ARTICLE; CATALYSIS; CATALYST; CONFORMATIONAL TRANSITION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033532320     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00145-7     Document Type: Article

References (24)

1. (a) Dervant, R. M.; Radunz, H. E. In Houben-Weyl; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E, 21 b, pp. 1314-1334.
2. (b) Soai, S.; Niwa, K. Chem. Rev. 1992, 92, 833.
3. (a) Singh, V. K. Synthesis 1992, 843.
4. (b) Deloux, L.; Screbnik, M. Chem. Rev. 1993, 93, 743.
5. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; chapter 5.
6. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
7. (c) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem., Int. Ed. Engl. 1990, 29, 205.
8. (c) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem., Int. Ed. Engl. 1990, 29, 205.
9. (d) Bringmann, G.; Breuning, M. Tetrahedron: Asymmetry 1998, 9, 667.
10. (e) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489.
11. (a) Fitzpatrick, K.; Hulst, R.; Kellogg, R. Tetrahedron: Asymmetry 1995, 6, 1861.
12. (b) Kellogg, R. M.; Hof, R. P. J. Chem. Soc., Perkin Trans, 1 1996, 1651.
13. (a) Gibson, C. L. Chem. Commun. 1996, 645.
14. (b) Fulton, D. A.; Gibson, C. L. Tetrahedron Lett. 1997, 38, 2019.
15. (c) Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1998, 9, 1409.
16. (d) Kang, J.; Lee, J. W.; Kim, J. I. J. Chem. Soc., Chem. Commun. 1994, 2009.
17. (e) Jin, M.; Ahn, S.; Lee, K. Tetrahedron Lett. 1996, 37, 8767.
18. (f) Rijnberg, E.; Jastrebski, J.; Janssen, M.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521.
19. (a) Wirth, T. Tetrahedron Lett. 1995, 36, 7849.
20. (b) Wirth, T.; Kulicke, K.; Fragale, G. Helv. Chim. Acta 1996, 79, 1957.
21. (c) Wessjohann, L. A.; Sinks, U. J. Prakt. Chem. 1998, 340, 189.
22. (a) Rozema, M. J.; Sidduri, A.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
23. (b) Knochel, P.; Perea, J.; Jones, P. Tetrahedron 1998, 54, 8275.
24. Confalone, P. N.; Pizzolato, G.; Baggiolini, E. G.; Lollar, D.; Uskokovic, M. R. J. Am. Chem. Soc. 1977, 99, 7020.