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    Rights statement: © Copyright 2018, Thieme Medical Publishers, Inc. All Rights Reserved

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Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles: Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles: Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity. / Kenny, Miles; Schröder, Sybrin; Taylor, Nicholas et al.
In: SYNTHESIS, Vol. 50, No. 9, 05.2018, p. 1796-1814.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Kenny, M, Schröder, S, Taylor, N, Jackson, P, Kitson, D & Franckevicius, V 2018, 'Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles: Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity', SYNTHESIS, vol. 50, no. 9, pp. 1796-1814. https://doi.org/10.1055/s-0036-1591957

APA

Kenny, M., Schröder, S., Taylor, N., Jackson, P., Kitson, D., & Franckevicius, V. (2018). Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles: Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity. SYNTHESIS, 50(9), 1796-1814. https://doi.org/10.1055/s-0036-1591957

Vancouver

Kenny M, Schröder S, Taylor N, Jackson P, Kitson D, Franckevicius V. Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles: Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity. SYNTHESIS. 2018 May;50(9):1796-1814. Epub 2018 Mar 27. doi: 10.1055/s-0036-1591957

Author

Kenny, Miles ; Schröder, Sybrin ; Taylor, Nicholas et al. / Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles : Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity. In: SYNTHESIS. 2018 ; Vol. 50, No. 9. pp. 1796-1814.

Bibtex

@article{de38c043b9884ca984d4bd54de2f0106,
title = "Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles: Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity",
abstract = "This article describes the palladium-catalysed three-component coupling of 1,3-dicarbonyl compounds with nucleophiles and propargylic electrophiles for the generation of quaternary all-carbon centres in a single step, which necessitates the simultaneous control of regio-, chemo- and enantioselectivity. The use of propargyl enol carbonates, the source of two of the components, was found to be essential in maintaining high levels of regiocontrol and chemoselectivity, whereas a careful analysis of pKa trends of O-, C- and N-nucleophiles as the other coupling partner indicates that the highest levels of selectivity are likely to be obtained with relatively acidic species, such as phenols, 1,3-dicarbonyl compounds and aromatic N-heterocycles. Finally, studies towards the development of the catalytic enantioselective construction of quaternary all-carbon centres by means of alkenylation and allylic alkylation are disclosed.",
keywords = "PALLADIUM, enantioselective catalysis, quaternary centres, propargylic electrophiles, 1,3-dicarbonyl compounds",
author = "Miles Kenny and Sybrin Schr{\"o}der and Nicholas Taylor and Paula Jackson and Daniel Kitson and Vilius Franckevicius",
note = "{\textcopyright} Copyright 2018, Thieme Medical Publishers, Inc. All Rights Reserved",
year = "2018",
month = may,
doi = "10.1055/s-0036-1591957",
language = "English",
volume = "50",
pages = "1796--1814",
journal = "SYNTHESIS",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "9",

}

RIS

TY - JOUR

T1 - Palladium-Catalysed Construction of All-Carbon Quaternary Centres with Propargylic Electrophiles

T2 - Challenges in the Simultaneous Control of Regio-, Chemo- and Enantioselectivity

AU - Kenny, Miles

AU - Schröder, Sybrin

AU - Taylor, Nicholas

AU - Jackson, Paula

AU - Kitson, Daniel

AU - Franckevicius, Vilius

N1 - © Copyright 2018, Thieme Medical Publishers, Inc. All Rights Reserved

PY - 2018/5

Y1 - 2018/5

N2 - This article describes the palladium-catalysed three-component coupling of 1,3-dicarbonyl compounds with nucleophiles and propargylic electrophiles for the generation of quaternary all-carbon centres in a single step, which necessitates the simultaneous control of regio-, chemo- and enantioselectivity. The use of propargyl enol carbonates, the source of two of the components, was found to be essential in maintaining high levels of regiocontrol and chemoselectivity, whereas a careful analysis of pKa trends of O-, C- and N-nucleophiles as the other coupling partner indicates that the highest levels of selectivity are likely to be obtained with relatively acidic species, such as phenols, 1,3-dicarbonyl compounds and aromatic N-heterocycles. Finally, studies towards the development of the catalytic enantioselective construction of quaternary all-carbon centres by means of alkenylation and allylic alkylation are disclosed.

AB - This article describes the palladium-catalysed three-component coupling of 1,3-dicarbonyl compounds with nucleophiles and propargylic electrophiles for the generation of quaternary all-carbon centres in a single step, which necessitates the simultaneous control of regio-, chemo- and enantioselectivity. The use of propargyl enol carbonates, the source of two of the components, was found to be essential in maintaining high levels of regiocontrol and chemoselectivity, whereas a careful analysis of pKa trends of O-, C- and N-nucleophiles as the other coupling partner indicates that the highest levels of selectivity are likely to be obtained with relatively acidic species, such as phenols, 1,3-dicarbonyl compounds and aromatic N-heterocycles. Finally, studies towards the development of the catalytic enantioselective construction of quaternary all-carbon centres by means of alkenylation and allylic alkylation are disclosed.

KW - PALLADIUM

KW - enantioselective catalysis

KW - quaternary centres

KW - propargylic electrophiles

KW - 1,3-dicarbonyl compounds

U2 - 10.1055/s-0036-1591957

DO - 10.1055/s-0036-1591957

M3 - Journal article

VL - 50

SP - 1796

EP - 1814

JO - SYNTHESIS

JF - SYNTHESIS

SN - 0039-7881

IS - 9

ER -