Asymmetric Organocatalytic Synthesis of trans-3,4-Disubstituted Isochromanones via an Intramolecular Aldol Reaction

Jeanne Fronert; Tom Bisschops; Elisa Cassens-Sasse; Iuliana Atodiresei; Dieter Enders

doi:10.1055/s-0033-1338742

Synthesis, Table of Contents

Synthesis 2013; 45(12): 1708-1712
DOI: 10.1055/s-0033-1338742

paper

Asymmetric Organocatalytic Synthesis of trans-3,4-Disubstituted Isochromanones via an Intramolecular Aldol Reaction

Jeanne Fronert

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 Email: enders@rwth-aachen.de

,

Tom Bisschops

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 Email: enders@rwth-aachen.de

,

Elisa Cassens-Sasse

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 Email: enders@rwth-aachen.de

,

Iuliana Atodiresei

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 Email: enders@rwth-aachen.de

,

Dieter Enders*

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Fax: +49(241)8092127 Email: enders@rwth-aachen.de

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Abstract

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Abstract

The diastereo- and enantioselective synthesis of 3-acetyl-4-hydroxyisochroman-1-ones via an intramolecular trans-selective aldol reaction employing proline-type organocatalysts is described. Good yields (64–88%) and high stereoselectivities (87 to >95% de, 84–99% ee) are obtained, thus potentially enabling, for example, a new direct entry to carbazolelactone alkaloid natural products.

Key words

organocatalysis - aldol reaction - asymmetric synthesis - dihydroisocoumarin - enamine activation

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References

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