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Synthesis 2011(24): 3979-3990  
DOI: 10.1055/s-0031-1289584
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Combinatorial Approach towards a Library of Chiral γ-Lactams and 2,3-Disubstituted Pyrroles

Tobias Biletzki, Wolfgang Imhof*
Friedrich-Schiller-University Jena, Institute of Inorganic and Analytical Chemistry, Humboldtstraße 8, 07743 Jena, Germany
Fax: +49(3641)948102; e-Mail: Wolfgang.Imhof@uni-jena.de;
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Publikationsverlauf

Received 20 July 2011
Publikationsdatum:
03. November 2011 (online)

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Abstract

A library of heterocyclic products with a wide variety of organic residues is produced via a four-component reaction of α,β-unsaturated aldehydes, primary amines, carbon monoxide, and ethylene using a multi-reactor station with an array of 96 autoclaves employing the same high-pressure reaction conditions for all catalytic reactions. In the presence of Ru3(CO)12 as a precatalyst, mixtures of chiral γ-lactams and 2,3-disubstituted pyrroles are obtained. This combinatorial approach also enables us for the first time to set up rules relating to the effects of specific substituents in the substrates on the outcome of the respective catalytic reaction.

Key words

ruthenium - C-H activation - catalysis - γ-lactams - pyrroles

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