INTEQUI 20941
INSTITUTO DE INVESTIGACIONES EN TECNOLOGIA QUIMICA
Unidad Ejecutora - UE
artículos
Título:
Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
Autor/es:
ALEJANDRO A. ORDEN; JOERG H. SCHRITTWIESER; VERENA RESCH; FRANCESCO G. MUTTI; WOLFGANG KROUTIL
Revista:
TETRAHEDRON-ASYMMETRY
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Lugar: Amsterdam; Año: 2013 vol. 24 p. 744 - 749
ISSN:
0957-4166
Resumen:
A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial w-transaminases, and the diastereoselective reduction of a Bischler Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomer.
