Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters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

Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters

Affiliation:	1. Unité de Chimie Organique associée au CNRS, Centre d''Etudes Pharmaceutiques, Université Paris-Sud, 5 rue J.-B. Clément, 92296 Châtenay-Malabry, France;2. I.C.S.N., CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France;1. Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran;2. Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran;1. Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;2. Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India;1. Radboud University Medical Center, Department of Internal Medicine, P.O. Box 9101, 6500 HB Nijmegen, The Netherlands;2. Bernard Nocht Institute for Tropical Medicine, WHO Collaborating Centre for Arbovirus and Haemorrhagic Fever Reference and Research, National Reference Centre for Tropical Infectious Diseases, Bernhard-Nocht Strasse 74, 20359 Hamburg, Germany;3. German Centre for Infection Research (DZIF), Partner Site Hamburg-Luebeck-Borstel, Hamburg, Inhoffenstraße 7, 38124 Braunschweig, Germany

Abstract:	Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct.

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