1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

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1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides. / Adcock, Holly V.; Langer, Thomas; Davies, Paul W.

In: Chemistry: A European Journal, Vol. 20, No. 24, 10.06.2014, p. 7262-7266.

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@article{2244200161c940be8eb25dfff569a69e,
title = "1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides",
abstract = "Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.",
keywords = "carbenes, cycloisomerisation, gold, regioselectivity, ynamides",
author = "Adcock, {Holly V.} and Thomas Langer and Davies, {Paul W.}",
year = "2014",
month = jun,
day = "10",
doi = "10.1002/chem.201403040",
language = "English",
volume = "20",
pages = "7262--7266",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "24",

}

RIS

TY - JOUR

T1 - 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

AU - Adcock, Holly V.

AU - Langer, Thomas

AU - Davies, Paul W.

PY - 2014/6/10

Y1 - 2014/6/10

N2 - Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.

AB - Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.

KW - carbenes

KW - cycloisomerisation

KW - gold

KW - regioselectivity

KW - ynamides

UR - http://www.scopus.com/inward/record.url?scp=84902108757&partnerID=8YFLogxK

U2 - 10.1002/chem.201403040

DO - 10.1002/chem.201403040

M3 - Article

C2 - 24828030

VL - 20

SP - 7262

EP - 7266

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 24

ER -