Polymer-supported N-tritylaziridinyl(diphenyl)methanol as an effective catalyst in the enantioselective addition of diethylzinc to aldehydes

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1095-1097

  Ten Holte, Peter ^a   Wijgergangs, Jan Piet ^a   Thijs, Lambertus ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000396681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990892b     Document Type: Article

References (19)

1. For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
2. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
3. (a) Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969.
4. (b) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489.
5. (c) Shi, M.; Satoh, Y.; Makihara, T.; Masaki, Y. Tetrahedron: Asymmetry 1995, 6, 2109.
6. (d) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
7. (a) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericàs, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309.
8. (b) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
9. (c) Watanabe, M.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1994, 837.
10. (d) Soai, K.; Watanabe, M.; Yamamoto, A. J. Org. Chem. 1990, 55, 4832.
11. (e) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140.
12. (a) Tanner, D.; Kornø, H. T.; Guijarro, D.; Andersson, P. G. Tetrahedron 1998, 54, 14232.
13. (b) Lawrence, C. F.; Nayak, S. K.; Thijs, L.; Zwanenburg, B. Synlett 1999, in press.
14. (a) Starmans, W. A. J.; Thijs, L.; Zwanenburg, B. Tetrahedron 1998, 54, 629.
15. (b) Willems, J. G. H.; Hersmis, M. C.; de Gelder, R.; Smits, J. M. M.; Hammink, J. B.; Dommerholt, F. J.; Thijs, L.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1997, 963 and references therein.
16. (c) Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 735 and references therein.
17. Triphenylchloromethane polymer bound, cross-linked with 1% DVB; 100-200 mesh, Fluka Chemika.
18. The resin was stirred for 15 min in a mixture of DCM/MeOH (1/1) containing an excess of base, according to a procedure by Barlos et al.: Barlos, K., Chatzi, O.; Gatos, D.; Stavropoulos, G. Int. J. Peptide Protein Res. 1991, 37, 513.
19. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.