Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

Grygorenko, Oleksandr O.; Kurkunov, Maksym; Levandovskiy, Igor A.; Tymtsunik, Andriy V.

doi:10.1055/s-0037-1609434

Cited by 5 publications

(1 citation statement)

References 48 publications

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“…A vast majority of the reported methods not only do not aim at the synthesis of pure enantiomer but even provide diastereomeric mixtures. A number of recent publications provide exceptions to one or both of the above points; − important (and already classical) examples include stereoisomeric 2-aminocyclobutanecarboxylic acids prepared and used by the groups of Ortuño, ,− Aitken, − Bolm, and others as the building blocks for the synthesis of peptidomimetics and organocatalysts.…”

Section: Introductionmentioning

confidence: 99%

Expanding the Chemical Space of 1,2-Difunctionalized Cyclobutanes

et al. 2023

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An efficient approach to the synthesis of previously unavailable or hardly accessible 1,2-difunctionalized cyclobutanes (mostly with NH 2 /NHBoc, OH, SH, or SO 2 F groups attached to the carbocycle either directly or via a CH 2 unit) relying on the divergent strategy is described. This class of compounds provides sp 3 -enriched and conformationally restricted building blocks that are of special demand for medicinal chemistry. The target compounds were prepared not only as pure racemic (±)-cis-and (±)-trans-diastereomers but in some cases also as single enantiomers. The developed procedures are readily scaled up and allow obtaining the target compounds on an up to hundred-gram scale. On the basis of the results of 20 X-ray diffraction experiments, structural characterization of the 1,2-difunctionalized cyclobutane core was performed using the extended Cremer−Pople puckering parameters and exit vector (EVP) plots.

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Section: Introductionmentioning

confidence: 99%

Expanding the Chemical Space of 1,2-Difunctionalized Cyclobutanes

et al. 2023

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

et al. 2019

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Nitrogen 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 (DERATma) as catalysts. FSA catalyzed most of the additions of ketones while DERATma 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%.

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Synthesis of saturated nitrogen heterocycles by Strecker reaction – nucleophilic cyclization

Grygorenko

2020

Tetrahedron Letters

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Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks

Cited by 5 publications

References 48 publications

Expanding the Chemical Space of 1,2-Difunctionalized Cyclobutanes

Expanding the Chemical Space of 1,2-Difunctionalized Cyclobutanes

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

Synthesis of saturated nitrogen heterocycles by Strecker reaction – nucleophilic cyclization

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