Stereoselective synthesis of the four stereoisomers of 4-(N,N- dibenzylamino)-2,2-dimethyl-3-hydroxypentanenitrile

Synthetic Communications

Volumn 27, Issue 18, 1997, Pages 3227-3234

  Moriarty, Robert M ^a,b   Tao, Anping ^a   Tuladhar, Sudersan M ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b Steroids Ltd   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (N,N DIBENZYLAMINO) 2,2 DIMETHYL 3 HYDROXYPENTANENITRILE; AMINOALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; POLYMERIZATION; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030849330     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004183     Document Type: Article

References (21)

1. (a) Knapp, S.; Hale, J. J. J. Org. Chem. 1993, 58, 2650.
2. (b) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
3. (c) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474.
4. Reetz, M. T.; Drewes, M. W.; Schmidtz, A. Angew. Chem. Int. Ed. Engl. 1987, 26, 1141.
5. (a) Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1976, 29, 97.
6. (b) Aoyagi, T.; Tobe, H.; Kojima, F.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1987, 31, 636.
7. (c) Herranz, R.; Castro-Pichel, J.; Garcia-Lopez, T. Synthesis 1989, 703.
8. (a) Umezawa, H. (ed.), Small Molecular Immunomodifiers of Microbial Origin. Fundamental and Clinical Studies of Bestatin. Japan Scientific Societies Press, Tokyo, and Pergamon Press, Oxford, 1981.
9. (b) Okura, A.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1988, 41, 261.
10. (c) Blomgren, H.; Wasserman, J. Cancer Lett. 1981, 11, 303.
11. (a) Perone, J. J.; Craik, C. S.; Fletterick, R. J. Science 1993, 261, 620.
12. (b) Singer, P. T.; Smalas, A.; Carty, R. P.; Mangel, W. F.; Sweet, R. M. Science 1993, 259, 669.
13. (c) Moriarty, R. M.; Liu, K.; Zhuang, H.; Lenz, D.; Brimfield, A.; Xia, C. Synth. Commun. 1995, 25, 2763.
14. Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556.
15. 1H NMR spectroscopy using (R)-(+)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (Mosher's acid) as a chiral solvating agent.
16. Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmidtz, A.; Holdgrun, X. Tetrahedron: Asymmetry 1990, 1, 375.
17. Moriarty, R. M.; Zhuang, H.; Penmasta, R.; Liu, K.; Awasthi, A. K.; Tuladhar, S. M.; Rao, M. S. C.; Singh, V. K. Tetrahedron Lett. 1993, 34, 8029.
18. (a) Freedman, J.; Vaal, M.J.; Huber, E.W. J. Org. Chem. 1991, 56, 670.
19. (b) Audia, J.E.; Colocci, N. Tetrahedron Lett. 1991, 32, 3779.
20. Poelert, M. A.; Hulshof, L. A.; Kellogg, R. M. Recueil des Travaux Chimiques des Pays Bas (Journal of the Royal Netherlands Chemical Society) 1994, 113, 355.
21. α-Amino aldehydes are relatively unstable both chemically and configurationally. They are notoriously prone to racemization during storage and during chromatography on silica gel (Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149).