Lactone Synthesis by Enantioselective Orthogonal Tandem Catalysis.
StackPhos
asymmetric catalysis
lactones
orthogonal tandem catalysis
synthetic methods
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 07 2019
08 07 2019
Historique:
received:
10
04
2019
revised:
08
05
2019
pubmed:
10
5
2019
medline:
15
9
2020
entrez:
10
5
2019
Statut:
ppublish
Résumé
In this work, we report enantioselective orthogonal tandem catalysis for the one pot conversion of Meldrum's acid derivatives and alkynes into δ-lactones. This new transformation, which resembles a formal [4+2] cycloaddition with concomitant decarboxylation and loss of acetone, proceeds in high yields and excellent enantioselectivity (up to 99 % ee) over a broad substrate scope. The products are densely functionalized and ripe for further transformations, as demonstrated here by both ring-opening reactions and reduction to saturated lactones. It was discovered that a new and serendipitously formed Ag
Identifiants
pubmed: 31071240
doi: 10.1002/anie.201904438
doi:
Substances chimiques
Lactones
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
9485-9490Subventions
Organisme : National Science Foundation
ID : CHE-1362498
Pays : International
Organisme : NIH HHS
ID : S10 OD021758
Pays : United States
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.