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Synfacts 2008(2): 0206-0206  
DOI: 10.1055/s-2007-992435
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Tandem Michael/Morita-Baylis-Hillman Reaction

Contributor(s): Benjamin List, Subhas Chandra Pan
S. Cabrera, J. Alemán, P. Bolze, S. Bertelsen, K. A. Jørgensen
Aarhus University, Denmark
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

An organocatalytic asymmetric tandem Michael/Morita-Baylis-Hillman reaction of α,β-unsaturated aldehydes 1 and Nazarov reagents 2 has been developed. Catalyst 4 in combination with benzoic acid was found to be effective for this reaction. With 10-20 mol% of catalyst 4, good to high diastereoselectivities (dr = 3:2 to 11:1) and excellent enantioselectivities (er = 93:7 to 99:1) are obtained for different α,β-unsaturated aldehydes.