Synthesis of Bridged Oxabicycles via Cascade Reactions involving O-Acyloxocarbenium Ion Intermediates.
Org Lett
; 23(21): 8312-8316, 2021 Nov 05.
Article
em En
| MEDLINE
| ID: mdl-34676754
ABSTRACT
Compared to related electrophilic species, O-acyloxocarbenium ions (AOIs) have been much less utilized in organic synthesis due to the lack of an efficient formation method. Here, we present a facile and simple approach for the generation of AOI from ester and acetal groups. Based on our AOI system with a pendant nucleophile, we obtained a unique bridged bicyclic system via an epoxonium-like transition state. The proposed mechanism is based on experimental and computational studies.
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MEDLINE
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En
Ano de publicação:
2021
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Article