Synfacts 2008(4): 0421-0421  
DOI: 10.1055/s-2008-1042828
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Applied Dienamine Catalysis

Contributor(s): Benjamin List, Corinna Reisinger
R. M. de Figueiredo, R. Fröhlich, M. Christmann*
RWTH Aachen and University of Münster, Germany
Further Information

Publication History

Publication Date:
19 March 2008 (online)


Cyclization of unsaturated dialdehydes 1 in the presence of a catalytic amount of chiral diphenylprolinol silyl ether 2 and benzoic acid led to the formation of highly enantioenriched bicyclic frameworks 3 (after reduction to the corresponding alcohols). Moreover, dienals 4 could be efficiently converted into monocyclic products 5. Both transformations rely on vinylogous en­amine activation of an enal as electron-rich dien­amine prone to undergo a rapid intramolecular Diels-Alder (IMDA) reaction or a vinylogous aldol condensation in the case of α-methylene aldehydes 4.