Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of gamma-, delta- and epsilon-Lactones

Danila Gasperini; Lorenzo Maggi; Stéphanie  Dupuy; Richard M. P.  Veenboer; David Cordes; Alexandra M.z. Slawin; Steven P. Nolan

doi:10.1002/adsc.201600575

Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of gamma-, delta- and epsilon-Lactones

Danila Gasperini, Lorenzo Maggi, Stéphanie Dupuy, Richard M. P. Veenboer, David Cordes, Alexandra M.z. Slawin, Steven P. Nolan

Department of Chemistry

University of St Andrews

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

40 Citations (SciVal)

Abstract

The improved synthesis of gamma-, delta- and epsilon-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to gamma- and delta-lactones in high regio- and stereoselectivity. Reactions were performed at low catalyst loadings and without the need for any additives. The use of a digold pre-catalyst provides a new synthetic route to functionalised epsilon-lactones, poorly accessible using previous methodologies.

Original language	English
Pages (from-to)	3857-3862
Number of pages	6
Journal	Advanced Synthesis & Catalysis
Volume	358
Early online date	23 Nov 2016
DOIs	https://doi.org/10.1002/adsc.201600575
Publication status	Published - 7 Dec 2016

Keywords

gold catalysis
lactones
low catalyst loading
NHC
solven-free

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https://risweb.st-andrews.ac.uk/portal/en/researchoutput/goldicatalysed-cyclisation-of-alkynoic-acids-towards-an-efficient-and-ecofriendly-synthesis-of---and-lactones(cb48270d-8ce9-4fb9-a0e8-3454ead22193)/export.html

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title = "Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of gamma-, delta- and epsilon-Lactones",

abstract = "The improved synthesis of gamma-, delta- and epsilon-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to gamma- and delta-lactones in high regio- and stereoselectivity. Reactions were performed at low catalyst loadings and without the need for any additives. The use of a digold pre-catalyst provides a new synthetic route to functionalised epsilon-lactones, poorly accessible using previous methodologies.",

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author = "Danila Gasperini and Lorenzo Maggi and St{\'e}phanie Dupuy and Veenboer, {Richard M. P.} and David Cordes and Slawin, {Alexandra M.z.} and Nolan, {Steven P.}",

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language = "English",

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T1 - Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of gamma-, delta- and epsilon-Lactones

AU - Gasperini, Danila

AU - Maggi, Lorenzo

AU - Dupuy, Stéphanie

AU - Veenboer, Richard M. P.

AU - Cordes, David

AU - Slawin, Alexandra M.z.

AU - Nolan, Steven P.

PY - 2016/12/7

Y1 - 2016/12/7

N2 - The improved synthesis of gamma-, delta- and epsilon-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to gamma- and delta-lactones in high regio- and stereoselectivity. Reactions were performed at low catalyst loadings and without the need for any additives. The use of a digold pre-catalyst provides a new synthetic route to functionalised epsilon-lactones, poorly accessible using previous methodologies.

AB - The improved synthesis of gamma-, delta- and epsilon-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to gamma- and delta-lactones in high regio- and stereoselectivity. Reactions were performed at low catalyst loadings and without the need for any additives. The use of a digold pre-catalyst provides a new synthetic route to functionalised epsilon-lactones, poorly accessible using previous methodologies.

KW - gold catalysis

KW - lactones

KW - low catalyst loading

KW - NHC

KW - solven-free

U2 - 10.1002/adsc.201600575

DO - 10.1002/adsc.201600575

M3 - Article

SN - 1615-4150

VL - 358

SP - 3857

EP - 3862

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

ER -

Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of gamma-, delta- and epsilon-Lactones

Abstract

Keywords

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