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An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles
Author(s) -
Ouchakour Lamiaa,
n Melinda,
Remete Attila M.,
Kiss Loránd
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100540
Subject(s) - chemistry , piperidine , ozonolysis , reductive amination , ring (chemistry) , amination , combinatorial chemistry , bond cleavage , stereochemistry , organic chemistry , catalysis
An improved, efficient synthesis of some functionalized saturated azaheterocycles has been accomplished by controlled functionalization of various readily available cyclic compounds containing ring C=C bond. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of various unsaturated scaffolds across ozonolysis followed by ring closing with double reductive amination with primary alkylamines or fluorinated alkylamines. The protocol provided versatile azaheterocyclic derivatives with a piperidine or azepane framework.