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

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

Liam M. Joyce
, Anthony C. Willis
, Christopher J.T. Hyland^*
, Stephen G. Pyne

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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 %).

Original language	English
Pages (from-to)	682-689
Number of pages	8
Journal	Australian Journal of Chemistry
Volume	71
Issue number	9
DOIs	https://doi.org/10.1071/CH18197
Publication status	Published - 2018

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title = "Gold- and Silver-Catalysed Cyclisation Reactions of β-Amino Allenes",

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 \%).",

author = "Joyce, \{Liam M.\} and Willis, \{Anthony C.\} and Hyland, \{Christopher J.T.\} and Pyne, \{Stephen G.\}",

note = "Publisher Copyright: {\textcopyright} 2018 CSIRO.",

year = "2018",

doi = "10.1071/CH18197",

language = "English",

volume = "71",

pages = "682--689",

journal = "Australian Journal of Chemistry",

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AU - Joyce, Liam M.

AU - Willis, Anthony C.

AU - Hyland, Christopher J.T.

AU - Pyne, Stephen G.

PY - 2018

Y1 - 2018

N2 - 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 %).

AB - 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 %).

UR - https://www.scopus.com/pages/publications/85052790179

U2 - 10.1071/CH18197

DO - 10.1071/CH18197

M3 - Article

SN - 0004-9425

VL - 71

SP - 682

EP - 689

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 9

ER -

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

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