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Synthesis 2018; 50(21): 4263-4269
DOI: 10.1055/s-0036-1589138
DOI: 10.1055/s-0036-1589138
feature
Acetic Anhydride Mediated Retro-Ene Reaction via a [4.4.3]Propellane Skeleton Intermediate Containing a Quaternary Ammonium Linkage
Further Information
Publication History
Received: 19 October 2017
Accepted: 26 October 2017
Publication Date:
13 December 2017 (online)
Published as part of the Special Section on the 26th French–Japanese Symposium on Medical and Fine Chemistry
Abstract
A novel retro-ene reaction via a [4.4.3]propellane intermediate containing a quaternary ammonium linkage was developed. The feature of this acetic anhydride mediated rearrangement includes the elimination of an acetoxy group at the C14 position and subsequent intramolecular nucleophilic addition of a nitrogen functional group to form an isolable ammonium salt intermediate. We clarified the reaction mechanism utilizing the deuterated derivative.
Key words
retro-ene - morphinan - [4.4.3]propellane - acetic anhydride - rearrangement - reaction mechanismSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589138.
- Supporting Information
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