Synlett 2024; 35(15): 1813-1816
DOI: 10.1055/a-2251-4145
letter

Synthesis and α-Functionalisation of Cyclic Imines

Ze Kuang
a   School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand
,
Xiao-Bo Ding
a   School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand
b   The Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand
,
a   School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand
b   The Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand
,
a   School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand
b   The Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand
› Institutsangaben
Financial support from the Maurice Wilkins Centre for Molecular Biodiscovery and the Royal Society Te Aparangi Marsdon Fund is gratefully acknowledged.


Abstract

α-Functionalisation of cyclic imines is explored. The cyclic imine substrates are synthesised from their respective halonitrile precursors using a nucleophilic addition/cyclisation sequence. Selective monohalogenation of the cyclic imines yields α-haloimines, which serve as a platform to obtain various α-hydroxyimine derivatives. In addition, an unusual tautomerisation and oxidation sequence is observed in the attempted preparation of α-hydroxyimines.

Supporting Information



Publikationsverlauf

Eingereicht: 16. November 2023

Angenommen nach Revision: 22. Januar 2024

Accepted Manuscript online:
22. Januar 2024

Artikel online veröffentlicht:
13. Februar 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany