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RESEARCH ARTICLE
Contents Vol 71(9)

Gold- and Silver-Catalysed Cyclisation Reactions of β-Amino Allenes

Liam M. Joyce A , Anthony C. Willis B , Christopher J. T. Hyland A C and Stephen G. Pyne A C
+ Author Affiliations
- Author Affiliations

A School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.

B Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia.

C Corresponding authors. Email: chrhyl@uow.edu.au; spyne@uow.edu.au

Australian Journal of Chemistry 71(9) 682-689 https://doi.org/10.1071/CH18197
Submitted: 2 May 2018  Accepted: 4 June 2018   Published: 3 July 2018

Abstract

Herein we report the formation of pyrrolines and tetrahydropyridines from the cyclisation reactions of β-amino allenes by both AuI and AgI catalysts in yields ranging from 5 to 70 %. AuI catalysts favour a 5-endo-dig cyclisation before rapid rearrangement to the 5-exo-dig product, while AgI favours a 6-endo-trig cyclisation. We also report the first known Ag2O catalysed cyclisation reaction of an allene which occurred in good yield (61 %).


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