Stereocontrolled Synthesis of Some Novel Azaheterocyclic β-Amino Ester Stereoisomers with Multiple Stereogenic Centers

Abstract The synthesis of some new functionalized azaheterocyclic β-amino esters with multiple stereocenters has been achieved from readily available unsaturated bicyclic β-amino acids by a stereocontrolled synthetic protocol involving N-allylation/propargylation, ring-opening metathesis, and select...

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Bibliographic Details
Published in:Synlett 2022-10, Vol.33 (16), p.1655-1659
Main Authors: Semghouli, Anas, Remete, Attila M., Novák, Tamás T., Kiss, Loránd
Format: Article
Language:English
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Summary:Abstract The synthesis of some new functionalized azaheterocyclic β-amino esters with multiple stereocenters has been achieved from readily available unsaturated bicyclic β-amino acids by a stereocontrolled synthetic protocol involving N-allylation/propargylation, ring-opening metathesis, and selective ring closure with chemodifferentiation through ring-closing metathesis (RCM). The RCM transformation was investigated under various experimental conditions to analyze the scope of the catalyst, yield, conversion, and substrate effect. The structure of the starting (oxa)norbornene β-amino acids predetermined the structure of the new azaheterocyclic derivatives; the synthetic procedure proceeded with conservation of the configuration of the stereogenic centers.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1877-3822