Synthesis of spirocyclic heterocycles from α,β-unsaturated N -acyliminium ions
Publication Name
Organic and Biomolecular Chemistry
Abstract
The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational studies provided mechanistic insights and an understanding of the stereochemical outcomes of these reactions.
Open Access Status
This publication is not available as open access
Volume
19
Issue
1
First Page
259
Last Page
272
Funding Number
DP130101968
Funding Sponsor
Australian Research Council