Intramolecular [2+2] photocycloaddition of substituted isoquinolones: Enantioselectivity and kinetic resolution induced by a chiral template

Kerrie A.B. Austin; Eberhardt Herdtweck; Thorsten Bach

doi:10.1002/anie.201103051

Intramolecular [2+2] photocycloaddition of substituted isoquinolones: Enantioselectivity and kinetic resolution induced by a chiral template

Kerrie A.B. Austin, Eberhardt Herdtweck, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

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

49 Scopus citations

Abstract

From simple to complex: Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88-96% ee) through the use of a chiral template. Compound 3, which was isolated in 53% ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process.

Original language	English
Pages (from-to)	8416-8419
Number of pages	4
Journal	Angewandte Chemie International Edition in English
Volume	50
Issue number	36
DOIs	https://doi.org/10.1002/anie.201103051
State	Published - 29 Aug 2011

Keywords

cycloaddition
enantioselectivity
hydrogen bonds
kinetic resolution
photochemistry

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abstract = "From simple to complex: Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88-96% ee) through the use of a chiral template. Compound 3, which was isolated in 53% ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process.",

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AU - Bach, Thorsten

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N2 - From simple to complex: Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88-96% ee) through the use of a chiral template. Compound 3, which was isolated in 53% ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process.

AB - From simple to complex: Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88-96% ee) through the use of a chiral template. Compound 3, which was isolated in 53% ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process.

KW - cycloaddition

KW - enantioselectivity

KW - hydrogen bonds

KW - kinetic resolution

KW - photochemistry

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M3 - Article

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ER -

Intramolecular [2+2] photocycloaddition of substituted isoquinolones: Enantioselectivity and kinetic resolution induced by a chiral template

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Keywords

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