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

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Published
<mark>Journal publication date</mark>9/10/2013
<mark>Journal</mark>Journal of the American Chemical Society
Volume135
Number of pages4
Pages (from-to)14948-14951
StatePublished
Early online date30/09/13
Original languageEnglish

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).