Asymmetric Strecker synthesis by addition of trimethylsilyl cyanide to aldehyde SAMP-hydrazones

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8479-8481

  Enders, Dieter ^a   Moser, Michael ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

1,2 addition; Asymmetric synthesis; Hydrazones; amino acids; amino nitriles

Indexed keywords

1 AMINO 2 METHOXYMETHYLPYRROLIDINE; ACID; ALDEHYDE; ALPHA AMINO ACID; CYANIDE; DICHLOROMETHANE; ETHER; HYDRAZONE DERIVATIVE; PYRROLIDINE DERIVATIVE; TITANIUM TETRACHLORIDE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOMER; HYDROLYSIS; ROOM TEMPERATURE; STRECKER SYNTHESIS;

EID: 0141991211     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.098     Document Type: Article

References (28)

1. Barrett G.C. Chemistry and Biochemistry of the Amino Acids. 1985;Chapman and Hall, London.
2. Williams R.M. Synthesis of Optically Active α-Amino Acids. 1989;Pergamon Press, Exeter.
3. Duthaler O.R. Tetrahedron. 50:1994;1539.
4. Strecker A. Liebigs. Ann. Chem. 75:1850;27.
5. Harada K. Nature (London). 200:1963;1201.
6. Harada K., Fox S.W. Naturwissenschaften. 51:1964;106.
7. Patel M.S., Worsley M. Can. J. Chem. 48:1970;1881.
8. Harada K., Okawara T. J. Org. Chem. 38:1973;707.
9. Ojima I., Inaba S. Chem. Lett. 1975;737.
10. Weinges K., Gries K., Stemmle B., Schrank W. Chem. Ber. 110:1977;2098.
11. Weinges K., Brune G., Droste H. Liebigs Ann. Chem. 1980;212.
12. Weinges K., Brachmann H., Stahnecker P., Rodewald H., Nixdorf M., Irngartinger H. Liebigs Ann. Chem. 1985;566.
13. Chakraborty T.K., Hussain K.A., Reddy G.V. Tetrahedron. 51:1995;9179.
14. Kunz, H.; Sager, W. Angew. Chem. 1987, 99, 595; Angew. Chem., Int. Ed. 1987, 26, 557.
15. Kunz H., Sager W., Pfrengle W., Schanzenbach D. Tetrahedron Lett. 29:1988;4397.
16. Kunz H., Pfrengle W. J. Am. Chem. Soc. 110:1988;651.
17. Davis F.A., Reddy R.E., Portonovo P.S. Tetrahedron Lett. 35:1994;9351.
18. Davis F.A., Portonovo P.S., Reddy R.E., Chiu Y. J. Org. Chem. 61:1996;440.
19. Choi J.Y., Kim Y.H. Tetrahedron Lett. 37:1996;7795.
20. For a review see: Enders D., Shilvock J.P. Chem. Soc. Rev. 29:2000;359.
21. Enders D., Eichenauer H. Chem. Ber. 112:1979;2933.
22. Review: Job A., Janeck C.F., Bettray W., Peters R., Enders D. Tetrahedron. 58:2002;2253.
23. Fernández, R.; Ferrete, A.; Lassaletta, J. M., Llera, J. M.; Monge, A. Angew. Chem. 2000, 112, 3015; Angew. Chem., Int. Ed. 2000, 39, 2893.
24. Enders D., Braig V., Raabe G. Can. J. Chem. 79:2001;1528.
25. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543.
26. 2, n-pentane/diethylether).
27. 3O: calcd 156.0899; found 156.0898.
28. All new compounds showed characteristic spectroscopic data (NMR, MS, IR) and correct HRMS or elemental analyses.