- Synthesis of optically active heterocyclic compounds by preparation of 1,3-dinitro derivatives and enzymatic enantioselective desymmetrization of prochiral diamines
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A general approach for the highly efficient chemical preparation of novel optically active 2-substituted propane-1,3-diamines is described. Diamines have been obtained from the corresponding commercially available aldehydes in a straightforward, two-step synthesis via the corresponding 1,3-dinitro compounds, which were hydrogenated under mild reaction conditions by using platinum dioxide as the catalyst. Subsequent enzymatic enantioselective desymmetrization mediated by Pseudomonas cepacia lipase allowed the recovery of a family of monocarbamates in good to high, enantiomeric excesses (70-90% ee).
- Rios-Lombardia, Nicolas,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
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scheme or table
p. 484 - 493
(2010/04/28)
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- Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds
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A wide range of prochiral 1, 3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates the high versatility and potential of this chemoenzymatic route as a source of intermediates in the synthesis of related optically active nitrogenated derivatives.
- Rios-Lombardia, Nicolas,Busto, Eduardo,Garcia-Urdiales, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
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supporting information; body text
p. 2571 - 2574
(2009/07/25)
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- First desymmetrization of 1,3-propanediamine derivatives in organic solvent. Development of a new route for the preparation of optically active amines
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The chemical synthesis and enzymatic desymmetrization of a panel of prochiral diamines have been successfully described for the first time using lipases in organic solvents. A family of 2-aryl-1,3-propanediamines has been obtained with high enantiopurity and good yields in the PSL-catalyzed reaction using diallyl carbonate in 1,4-dioxane.
- Bustos, Eduardo,Gotor-Fernandez, Vicente,Montejo-Bernardo, Jose,Garcia-Granda, Santiago,Gotor, Vicente
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p. 4203 - 4206
(2008/02/14)
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- Synthesis and Antidepressant Profiles of Phenyl-Substituted 2-Amino- and 2--1,4,5,6-tetrahydropyrimidines
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A series of 4(6)- and 5-phenyl-substituted 2-amino- and 2-(alkoxycarbonyl)amino-1,4,5,6-tetrahydropyrimidines 2 were prepared and evaluated for central nervous system (CNS) effects in animal models.Several 5-phenyl-substituted compounds possessed potent
- Weinhardt, Klaus,Wallach, Marshall B.,Marx, Michael
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p. 694 - 698
(2007/10/02)
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- 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives
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Certain 1,4,5,6-tetrahydropyrimidine compounds which are substituted with an amino, amido or carbamate at the 2-position, with an optionally substituted phenyl at the 5-position or at the 4-position when there is no alkyl at the 1-position and optionally
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