Title

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

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Link to publisher version (DOI)

http://dx.doi.org/10.1039/d0ob02075c