Enantiopure N-ferrocenylmethylaziridin-2-ylmethanols from L-serine: Synthesis, crystal structure and applications

Tetrahedron Asymmetry

Volumn 15, Issue 8, 2004, Pages 1289-1294

  Wang, Min Can ^a   Wang, De Kun ^a   Zhu, Yu ^a   Liu, Lan Tao ^a   Guo, Yi Fei ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CARBOXYL GROUP; CHLORIDE; ESTER DERIVATIVE; FERROCENE DERIVATIVE; LIGAND; METHANOL DERIVATIVE; METHYL GROUP; N FERROCENYLMETHYLSERINE METHYL ESTER; TOLUENE; TOLUENESULFONYL CHLORIDE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; ENERGY YIELD; GRIGNARD REACTION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; X RAY ANALYSIS;

EID: 1842636571     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.02.013     Document Type: Article

References (37)

1. Tanner D., Andersson P.G., Harden A., Somfai P. Tetrahedron Lett. 35:1994;4631.
2. Andersson P.G., Harden A., Tanner D., Norrby P.-O. Chem. Eur. J. 1:1995;12.
3. Willems J.G.H., de Vries J.G., Nolte R.J.M., Zwanenburg B. Tetrahedron Lett. 36:1995;3917.
4. Willems J.G.H., Dommerholt F.J., Hamink J.B., vaarhorst A.M., Thijs L., Zwanenburg B. Tetrahedron Lett. 36:1995;603.
5. Andersson P.G., Guijarro D., Tanner D. J. Org. Chem. 62:1997;7364.
6. Tanner D., Kornø H.T., Guijarro D., Andersson P.G. Tetrahedron. 54:1998;14213.
7. Lawrence C.F., Nayak S.K., Thijs L., Zwanenburg B. Synlett. 1999;1571.
8. Ten Holte P., Wijgergangs J.-P., Thijs L., Zwanenburg B. Org. Lett. 1:1999;1095.
9. Shadakshari U., Nayak S.K. Tetrahedron. 57:2001;8185.
10. Shi M., Jiang J.-K., Feng Y.-S. Tetrahedron: Asymmetry. 11:2000;4923.
11. Bulman Page P.C., Allin S.M., Maddocks S.J., Elsegood M.R.J. J. Chem. Soc. Perkin Trans. 1. 2002;36:2827.
12. For general reviews, see: Noyori R., Kitamura M. Angew. Chem. Int. Ed. Engl. 30:1991;49.
13. Soai K., Niwa S. Chem. Rev. 92:1992;833.
14. Pu L., Yu H.-B. Chem. Rev. 101:2001;757.
15. For reviews, see: Dai L.-X., Tu T., You S.-L., Deng W.-P., Hou X.-L. Acc. Chem. Res. 36:2003;659.
16. Sutcliffe O.B., Bryce M.R. Tetrahedron: Asymmetry. 14:2003;2297.
17. Colacot T.J. Chem. Rev. 103:2003;3101.
18. Sato K., Kozikowski A.P. Tetrahedron Lett. 30:1989;4073.
19. Baldwin J.E., Adlington R.M., Robinson N.G. J. Chem. Soc., Chem. Commun. 1987;153.
20. Okawa K., Nakajima K. Biopolymers. 20:1981;1811.
21. Tanaka T., Okawa K., Nakajima K. Bull. Chem. Soc. Jpn. 53:1980;1352.
22. Cainelli G., Panunzio M. Tetrahedron Lett. 32:1991;121.
23. Cerhart F., Higgins W., Tardif C., Ducep J.B. J. Med. Chem. 33:1990;2157.
24. Tanner D. Angew. Chem. Int. Ed. Engl. 33:1994;599.
25. Kornm A., Rudolph-Böhner S., Moroder L. Tetrahedron. 50:1994;1717.
26. Okawa K., Nakajima K., Tanaka T. J. Synth. Org. Chem. Jpn. 42:1984;390.
27. Smrt J., Beranek J., Sicher J. Chem. Abstr. 55:1961;10468i.
28. Wenker H. J. Am. Chem. Soc. 57:1935;2328.
29. Nakajima K., Takai F., Tanaka T., Okawa K. Bull. Chem. Soc. Jpn. 51:1978;1577.
30. Nadagawa Y., Tsuno T., Nakajima K., Iwai M., Kawai H. Bull. Chem. Soc. Jpn. 45:1972;1162.
31. Häner R., Olano B., Seebach D. Helv. Chim. Acta. 70:1987;1676.
32. Kuyl-Yeheskiely E., Lodder M., van der Marel G.A., van Boom J.H. Tetrahedron Lett. 33:1992;3013.
33. Willems J.G.H., Hersmis M.C., de Gelder R., Smits J.M.M., Hamink J.B., Dommerholt F.J., Thijs L., Zwanenburg B. J. Chem. Soc., Perkin Trans. 1. 1997;963.
34. Muchow G., Vannoorenberghe Y., Buono G. Tetrahedron Lett. 28:1987;6163.
35. Watanabe M., Araki S., Butsugan Y., Uemura M. Chem. Express. 5:1990;661.
36. Wu Y.-J., Yun H.-Y., Wu Y.-S., Ding K.-L., Zhou Y. Tetrahedron: Asymmetry. 11:2000;3543.
37. The reaction was monitored by TLC.