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Synthesis 2014; 46(06): 799-808
DOI: 10.1055/s-0033-1340565
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© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Synthesis of Functionalized 1,3,5-Triarylpyrrolidin-2-ones via an Aza-Michael/Aldol Domino Reaction

Céline Joie
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Fax: +49(241)8092127   Email: enders@rwth-aachen.de
,
Kristina Deckers
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
› Author Affiliations
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Publication History

Received: 10 December 2013

Accepted: 13 December 2013

Publication Date:
09 January 2014 (online)

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Abstract

The organocatalytic asymmetric synthesis of functionalized 1,3,5-triarylpyrrolidin-2-ones bearing three contiguous stereocenters through an aza-Michael/aldol domino reaction of α-ketoamides with α,β-unsaturated aldehydes is described. The domino products were further derivatized by aldehyde olefination under one-pot conditions. The reaction proceeds with excellent diaste­reoselectivities (>20:1) and good to excellent enantioselectivities (60–96% ee).

Key words

organocatalysis - domino reactions - asymmetric synthesis - pyrrolidin-2-ones - aza-Michael addition

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