Enzyme catalysed asymmetrization of pyridyl substituted 1,3-propanediols and of the corresponding diacetates

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2175-2187

  Guanti, Giuseppe ^a   Narisano, Enrica ^a   Riva, Renata ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PROPANEDIOL DERIVATIVE; PYRIDINE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030796611     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00218-8     Document Type: Article

References (33)

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21. 4: Lipp, A.; Zirngibl, E. Chem. Ber. 1906, 39, 1045-1054; 1: Gangrkii, P. A.; Chvyreva, E. G.; Chumakov, Y. I. Med. Prom. S.S.S.R. 1959, 13, 13-15; Chem Abs. 54, 18512e.
22. 4: Lipp, A.; Zirngibl, E. Chem. Ber. 1906, 39, 1045-1054; 1: Gangrkii, P. A.; Chvyreva, E. G.; Chumakov, Y. I. Med. Prom. S.S.S.R. 1959, 13, 13-15; Chem Abs. 54, 18512e.
23. We also observed that the resolution of monoacetate 2 (e.e. 88%) catalysed by supported PPL and performed following conditions used in entry 3 (Table 2), is very efficient and the e.e. have been enhanced to 97.5%, after a 4.5% conversion.
24. PPL catalysed acetylation of 4 was already reported (Cesti, P.; Zaks, A.; Klibanov, A. M. Appl. Biochem. Biotechnol. 1985, 11, 401-407). However the e.e. was not determined.
25. Guanti, G.; Riva, R. unpublished results.
26. We have already demonstrated that in monohydrolysis of a some diesters, using PLE as enzyme, the rate and the enantioselectivity are strongly influenced by the presence of an organic co-solvent (Ref. Guanti, G.; Banfi, L.; Narisano, E.; Riva, R.; Thea, S. Tetrahedron Lett. 1986, 27, 4639-4642).
27. Authors of Ref. 4d experienced the same behaviour during the hydrogenation of 1 to give the corresponding pyperidine diol; that's the reason why they prepared that diol using a completely different approach.
28. To prevent this undesired process, usually the hydrogenation is conduced in the presence of an acid (Ref. Keay, J. in Comprehensive Organic Synthesis, Trost, B. M. Ed. 1991, vol. 8, 579-602, Pergamon Press, Oxford).
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31. b) Azzena, U.; Chelucci, G.; Delogu, G.; Gladiali, S.; Marchetti, M.; Soccolini, F.; Botteghi, C. Gazz. Chim. Ital. 1986, 116, 307-315.
32. D of this was lower than the one reported, but, due to the volatility of this compound, we did not strip away all the solvent.
33. Some preliminary results were already presented in the symposium: Biocatalisi e Sintesi Organica, Acquafredda di Maratea (I), 1996, May, 3-5.