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Synlett
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
,
Daniel P. Furkert 
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
,
Margaret A. Brimble  ∗
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
› Author AffiliationsFinancial support from the Maurice Wilkins Centre for Molecular Biodiscovery and the Royal Society Te Aparangi Marsdon Fund is gratefully acknowledged.
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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.

Key words

cyclic imine - spiroimine - α-functionalisation - α-hydroxyimine - α-bromoimine

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2251-4145.
  • Supporting Information


Publication History

Received: 16 November 2023

Accepted after revision: 22 January 2024

Accepted Manuscript online:
22 January 2024

Article published online:
13 February 2024

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