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Synfacts 2009(7): 0791-0791  
DOI: 10.1055/s-0029-1217309
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Diels-Alder Reaction in Seawater

Contributor(s): Benjamin List, Frank Lay
D.-Q. Xu, A.-B. Xia, S.-P. Luo, J. Tang, S. Zhang, J.-R. Jiang, Z.-Y. Xu*
Zheijiang University of Technology, Hangzhou, P. R. of China
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The authors present an asymmetric Diels-Alder reaction of cyclohexenones with nitroolefins. Employing amine catalyst 1 and 4-(tri­fluoromethyl)benzoic acid as additive the desired Diels-Alder adducts were obtained in good to ­excellent yields and high diastereo- and enantio-selectivities. The postulated mechanism proceeds via in situ enamine activation involving a one-step concerted addition pathway. Enamines intermediates proposed in the catalytic cycle have been confirmed by ESI-MS.