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Synfacts 2008(12): 1328-1328  
DOI: 10.1055/s-0028-1087336
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Noyori Ligand as Organocatalyst

Contributor(s): Benjamin List, Corinna Reisinger
Y.-D. Ju, L.-W. Xu*, L. Li, G.-Q. Lai*, H.-Y. Qiu, J.-X. Jiang, Y. Lu
Hangzhou Normal University, Lanzhou Institute of Chemical Physics, P. R. of China and National University of Singapore, Republic of Singapore
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

The present work reveals the mono-sulfonyl diamine Ts-DPEN 3 as an effective catalyst for the asymmetric Michael addition of ­cyclic β-keto ester 2 to aromatic nitroolefins 1. The corresponding Michael adducts 4 were obtained in good yields with moderate to good diastereo- and enantioselectivities. The authors propose the simultaneous activation of both reaction partners via multiple H-bonds as the catalytic reaction mode. However, alternative mechanisms, for example invoking enamine activation, may also be considered (see scheme).