Intramolecular [2+2] Cycloadditions of α‐Heteroatom Substituted γ,δ‐Unsaturated Ketenes
Journal
Asian Journal of Organic Chemistry
ISSN
2193-5807
2193-5815
2193-5815
Date Issued
2024-08-13
Author(s)
Abstract
An improved synthetic procedure for the intramolecular ketene [2+2] cycloaddition was developed for the preparation of 1-heteroatom-substituted bicyclo[2.1.1]hexan-5-ones. It was found that the use of the Mukaiyama reagent (2-chloro-N-methyl-pyridinium iodide) was key to efficiently generate the α-heteroatom substituted homoallyl ketene intermediate for the cycloaddition reaction. The synthetic utility of the resulting bicyclic ketone was demonstrated through the preparation of a saturated variant of vortioxetine.
Subjects
Cycloaddition
Isosteres
Ketene
Synthetic Methods
SDGs
Publisher
Wiley
Type
journal article