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Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template

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Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template. / Coote, Susannah; Bach, Thorsten.

In: Journal of the American Chemical Society, Vol. 135, 09.10.2013, p. 14948-14951.

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Coote, Susannah ; Bach, Thorsten. / Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template. In: Journal of the American Chemical Society. 2013 ; Vol. 135. pp. 14948-14951.

Bibtex

@article{0fe8d64b9d484c0c9277dd3340f61111,
title = "Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template",
abstract = "The first examples of enantioselective intermolecular [2+2] photocycloadditions of isoquinolone with alkenes are reported. Photoreactions were carried out at low temperature in the presence of a chiral hydrogen-bonding template, which effectively shields one face of the substrate through formation of a hydrogen-bonded supramolecular complex. Functionalized cyclobutane products were obtained in excellent yields (86−98{\%}) and with outstanding regio-, diastereo-, and enantioselectivity (88−99{\%} ee).",
keywords = "Photochemistry, Enantioselectivity, [2+2] Photocycloaddition",
author = "Susannah Coote and Thorsten Bach",
year = "2013",
month = "10",
day = "9",
doi = "10.1021/ja408167r",
language = "English",
volume = "135",
pages = "14948--14951",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "AMER CHEMICAL SOC",

}

RIS

TY - JOUR

T1 - Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template

AU - Coote, Susannah

AU - Bach, Thorsten

PY - 2013/10/9

Y1 - 2013/10/9

N2 - The first examples of enantioselective intermolecular [2+2] photocycloadditions of isoquinolone with alkenes are reported. Photoreactions were carried out at low temperature in the presence of a chiral hydrogen-bonding template, which effectively shields one face of the substrate through formation of a hydrogen-bonded supramolecular complex. Functionalized cyclobutane products were obtained in excellent yields (86−98%) and with outstanding regio-, diastereo-, and enantioselectivity (88−99% ee).

AB - The first examples of enantioselective intermolecular [2+2] photocycloadditions of isoquinolone with alkenes are reported. Photoreactions were carried out at low temperature in the presence of a chiral hydrogen-bonding template, which effectively shields one face of the substrate through formation of a hydrogen-bonded supramolecular complex. Functionalized cyclobutane products were obtained in excellent yields (86−98%) and with outstanding regio-, diastereo-, and enantioselectivity (88−99% ee).

KW - Photochemistry

KW - Enantioselectivity

KW - [2+2] Photocycloaddition

U2 - 10.1021/ja408167r

DO - 10.1021/ja408167r

M3 - Journal article

VL - 135

SP - 14948

EP - 14951

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

ER -