Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
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 ami...
| Autores: | , , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2013 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/2208 |
| Acesso em linha: | http://hdl.handle.net/11336/2208 |
| Access Level: | acceso abierto |
| Palavra-chave: | Chemoenzymatic Alkaloids Transaminases Stereoselectivity https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Resumo: | 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 x-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. |
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