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Title

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

AuthorsRoldán, Raquel; Hernández Sánchez, Karel ; Joglar, Jesús; Bujons, Jordi; Parella, Teodor; Fessner, Wolf Dieter; Clapés, Pere
KeywordsAldolases
Aldol reaction
Biocatalysis
Nitrogen heterocycles
Reductive amination
Issue Date28-Jan-2019
PublisherWiley-Blackwell
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
URIhttp://hdl.handle.net/10261/180011
DOI10.1002/adsc.201801530
Appears in Collections:(IQAC) Artículos
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