Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid-Derived Nitriles

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Journal Title
Journal ISSN
Volume Title
A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Date
2023-01-03
Major/Subject
Mcode
Degree programme
Language
en
Pages
7
1512-1518
Series
Synlett, Volume 34, issue 12
Abstract
Novel, substituted chromenopyrrolidininones have been synthesized from natural amino acid derivatives through an unprecedented sequence involving a Knoevenagel-Transesterification sequence and an allylative palladium-catalyzed cyclization reaction. The products are nature-inspired heterocycles derived from natural amino acids. The targets could be synthesized with varying degrees of stereoselectivity: racemization is a known issue with amino acids and provided a formidable challenge to our method development, as well. Altogether, six derivatives were synthesized with yields from moderate to good.
Description
Publisher Copyright: © 2022 Georg Thieme Verlag. All rights reserved.
Keywords
5-endo-Trig, Amino acid racemization, Chromenopyrrolidine, Coumarin, Pyrrolidinone
Other note
Citation
Heikinheimo , A , Nieger , M & Koskinen , A M P 2023 , ' Diastereoselective Synthesis of Substituted Chromenopyrrolidinones from Amino Acid-Derived Nitriles ' , Synlett , vol. 34 , no. 12 , pp. 1512-1518 . https://doi.org/10.1055/a-1992-6650