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

Liam M. Joyce; Anthony C. Willis; Christopher J. T. Hyland; Stephen G. Pyne

doi:10.1071/CH18197

RESEARCH ARTICLE

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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 Au^I and Ag^I catalysts in yields ranging from 5 to 70 %. Au^I catalysts favour a 5-endo-dig cyclisation before rapid rearrangement to the 5-exo-dig product, while Ag^I 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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Gold- and Silver-Catalysed Cyclisation Reactions of β-Amino Allenes

Abstract

References

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