Enantioselective phase transfer catalyzed synthesis of spirocyclic azetidine oxindoles
Author(s)
Type
Journal Article
Abstract
Spiro-3,2’-azetidine oxindoles combine two independently important pharmacophores in an understudied spirocyclic motif that is attractive for medicinal chemistry. Here, the enantioselective synthesis of these structures is achieved in ers of up to 2:98 through intramolecular C–C bond formation, involving activation of the substrate with a novel SF5-containing chiral cation phase transfer (PT) catalyst. The products are readily elaborated/deprotected to afford medicinally relevant enantioen-riched compounds. Control experiments suggest an interfacial PT mechanism, whereby catalytic asymmetric induction is achieved through activation of the chloride leaving group.
Date Issued
2024-03-15
Date Acceptance
2024-03-04
Citation
Organic Letters, 2024, 26 (10), pp.2079-2084
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
2079
End Page
2084
Journal / Book Title
Organic Letters
Volume
26
Issue
10
Copyright Statement
© 2024 The Authors. Published by American Chemical Society. This publication is licensed under
CC-BY 4.0.
CC-BY 4.0.
License URL
Identifier
https://pubs.acs.org/doi/10.1021/acs.orglett.4c00358
Publication Status
Published
Date Publish Online
2024-03-06