Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes...

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Detalles Bibliográficos
Autores principales: Demming, Rebecca M., Hammer, Stephan C., Nestl, Bettina M., Gergel, Sebastian, Fademrecht, Silvia, Pleiss, Jürgen, Hauer, Bernhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471033/
https://www.ncbi.nlm.nih.gov/pubmed/30256501
http://dx.doi.org/10.1002/anie.201810005
Descripción
Sumario:The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale.

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