Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: preparation of valuable nitrogenated compounds.
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.
Ríos-Lombardía
Nicolás
N
Departamento de Quimica Organica e Inorganica, Instituto Universitario de Biotecnologia de Asturias, Universidad de Oviedo, c/Julian Claveria s/n Oviedo 33071, Spain.
Busto
Eduardo
E
García-Urdiales
Eduardo
E
Gotor-Fernández
Vicente
V
Gotor
Vicente
V
D016956:Burkholderia cepacia / Q000201:enzymology; D003959:Diamines / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism*; D009904:Optical Rotation
D003959:Diamines; D008049:Lipase