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

Coote, Susannah and Bach, Thorsten (2013) Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template. Journal of the American Chemical Society, 135. pp. 14948-14951. ISSN 0002-7863

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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).

Item Type:
Journal Article
Journal or Publication Title:
Journal of the American Chemical Society
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1503
Subjects:
ID Code:
72296
Deposited By:
Deposited On:
05 Jan 2015 14:41
Refereed?:
Yes
Published?:
Published
Last Modified:
13 May 2020 02:44