jo8025912_si_001.pdf (2.63 MB)
Enzymatic Desymmetrization of Prochiral 2-Substituted-1,3-Diamines: Preparation of Valuable Nitrogenated Compounds
journal contribution
posted on 2009-03-20, 00:00 authored by Nicolás Ríos-Lombardía, Eduardo Busto, Eduardo García-Urdiales, Vicente Gotor-Fernández, Vicente GotorA 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.
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reaction conditionsprochiraldiamineFinalcarbamatealkoxycarbonylating agentnitrogenated derivativessourcemoietySubstituteddiallyl carbonatesynthesisPreparationPseudomonas cepaciacatalystintermediateversatilitylipaseValuable Nitrogenated CompoundsEnzymatic DesymmetrizationProchiraldesymmetrizedcleavagechemoenzymatic route
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