Synthesis of β-Amino Acid Derivatives via Enantioselective Lewis Base Catalyzed N-Allylation of Halogenated Amides with Morita-Baylis-Hillman Carbonates.
β-amino acid * Lewis base catalysis * Morita Baylis Hillman adducts * enantioselective synthesis * spiro compounds
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
20 Dec 2023
20 Dec 2023
Historique:
revised:
18
12
2023
received:
01
12
2023
accepted:
19
12
2023
medline:
20
12
2023
pubmed:
20
12
2023
entrez:
20
12
2023
Statut:
aheadofprint
Résumé
Trifluoro- and trichloroacetamides serving as pronucleophiles undergo enantioselective Lewis base catalyzed N-allylation with Morita-Baylis-Hillman carbonates to produce enantioenriched β-amino acid derivatives. The reactions proceed as a kinetic resolution to give the allylation products and the remaining carbonates in good yields and high enantioselectivity. The obtained products are amenable to diastereoselective derivatization to produce a library of spiro-isoxazoline lactams.
Identifiants
pubmed: 38116835
doi: 10.1002/chem.202304014
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202304014Informations de copyright
© 2023 Wiley-VCH GmbH.