English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/180011
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:


Aldolase-Catalyzed Asymmetric Synthesis of N-Heterocycles by Addition of Simple Aliphatic Nucleophiles to Aminoaldehydes

AuthorsRoldán, Raquel; Hernández Sánchez, Karel ; Joglar Tamargo, Jesús ; Bujons, Jordi; Parella, Teodor; Fessner, Wolf Dieter; Clapés Saborit, Pere
Aldol reaction
Nitrogen heterocycles
Reductive amination
Issue Date28-Jan-2019
CitationAdvanced Synthesis and Catalysis (2019)
AbstractNitrogen heterocycles are structural motifs found in many bioactive natural products and of utmost importance in pharmaceutical drug development. In this work, a stereoselective synthesis of functionalized N-heterocycles was accomplished in two steps, comprising the biocatalytic aldol addition of ethanal and simple aliphatic ketones such as propanone, butanone, 3-pentanone, cyclobutanone, and cyclopentanone to N-Cbz-protected aminoaldehydes using engineered variants of d-fructose-6-phosphate aldolase from Escherichia coli (FSA) or 2-deoxy-d-ribose-5-phosphate aldolase from Thermotoga maritima (DERA Tma ) as catalysts. FSA catalyzed most of the additions of ketones while DERA Tma was restricted to ethanal and propanone. Subsequent treatment with hydrogen in the presence of palladium over charcoal, yielded low-level oxygenated N-heterocyclic derivatives of piperidine, pyrrolidine and N-bicyclic structures bearing fused cyclobutane and cyclopentane rings, with stereoselectivities of 96–98 ee and 97:3 dr in isolated yields ranging from 35 to 79%. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Publisher version (URL)https://doi.org/10.1002/adsc.201801530
Appears in Collections:(IQAC) Artículos
Show full item record
Review this work

Related articles:

WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.