Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Enantioselective Michael addition of malonates to aromatic nitroalkenes catalyzed by monosaccharide-based chiral crown ethers

Affiliation:	1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, 1521 Budapest, Hungary;2. Organic Chemical Technology Research Group of the Hungarian Academy of Sciences, Budapest, Hungary;3. Chemical Research Institute for Chemistry, Hungarian Academy of Sciences, H-1525 Budapest, Hungary;1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, PO Box 91, H-1521 Budapest, Hungary;2. ‘Lendület’ Supramolecular Chemistry Research Group, Institute of Organic Chemistry, Research Centre of Natural Sciences, Hungarian Academy of Sciences, PO Box 286, H-1519 Budapest, Hungary;1. Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland;2. SRSMC, Nancy Universite & CNRS, Faculte des Sciences et Techniques, B. 70239, F-54506 Vandoeuvre-les-Nancy Cedex, France;1. Faculdade de Ciências Farmacêuticas de Ribeirão Preto, USP, Av. Café S/N, CEP 14040-903, Ribeirão Preto, SP, Brazil;2. Department of Biological Chemistry, John Innes Centre, Norwich Research Park, Norwich NR4 7UH, UK;3. Faculdade de Medicina de Ribeirão Preto, Department of Parasitology Microbiology and Immunology, USP, Av. Bandeirantes 3900, CEP 14049-900, Ribeirão Preto, SP, Brazil;4. Department of Microbiology, Immunology and Parasitology, Universidade Federal de São Paulo, Rua Botucatu 862 8, Andar 04023-062, São Paulo, SP, Brazil

Abstract:	The asymmetric Michael addition of diethyl malonate and α-substituted diethyl malonates to aromatic nitroalkenes was carried out under mild reaction conditions in a solid–liquid phase transfer reaction in the presence of α-d-glucopyranoside- and α-d-mannopyranoside-based crown ethers as the catalysts. The use of d-glucose-based lariat ether 1 gave the best results. The substituents of the β-nitrostyrene and the diethyl malonate had a significant impact on the chemical yields and enantioselectivity. The addition of diethyl-2-acetamidomalonate to aromatic nitroalkenes afforded the corresponding Michael adducts in moderate to high enantiomeric excess (ee up to 99%). The reaction of diethyl-2-methylmalonate with 2-nitro-β-nitrostyrene gave the adduct with 93% enantiomeric excess in the presence of crown catalyst 1.

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