Synfacts 2008(2): 0197-0197  
DOI: 10.1055/s-2007-992432
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Diels-Alder Reaction of Nitroolefins

Contributor(s): Benjamin List, Corinna Reisinger
H. Sundén, R. Rios, Y. Xu, L. Eriksson, A. Córdova*
Stockholm University, Sweden
Further Information

Publication History

Publication Date:
23 January 2008 (online)


The diastereoselective and enantio­selective formation of bicyclic Diels-Alder products 4 starting from α,β-unsaturated cyclic ketones 1 of different ring sizes and (hetero)aromatic nitroolefins 2 is described. Aliphatic nitroolefins give only traces of product. Commercially available, chiral diamine 3 in combination with DNBSA was used as catalyst. In accordance with the observed absolute stereochemistry, the reaction is suggested to proceed via a stepwise domino double Michael addition pathway. Alternatively, a concerted Diels-Alder mechanism may be considered.