Synthesis of spirocyclic heterocycles from α,β-unsaturated N -acyliminium ions

Authors

Thanphat Thaima, University of Wollongong
Arife Yazici, University of Wollongong
Chiramet Auranwiwat, University of Wollongong
Anthony C. Willis, The Australian National University
Uta Wille, Bio21 Molecular Science and Biotechnology Institute
Thunwadee Limtharakul, Chiang Mai University
Stephen G. Pyne, University of Wollongong

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