A highly regio- and enantioselective organocatalyzed Michael addition of malonates to nitrodienes |
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| Institution: | 1. Laboratory of Inorganic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, GR-54124 Thessaloniki, Greece;2. Laboratory of Organic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, GR-54124 Thessaloniki, Greece;1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. UMR 6226 CNRS-Université de Rennes 1, Institut des Sciences Chimiques de Rennes, Organométalliques: Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes, France;3. Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510, USA |
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| Abstract: | An organocatalyzed direct Michael addition of unsubstituted/substituted malonates, acetoacetate, or acetylacetones to conjugated nitrodienes using a cinchona alkaloid-based thiourea catalyst is disclosed. The addition products were formed in high yields and regioselectivity. The enantioselectivities of the addition products were high in most cases and could significantly be improved upon by a single recrystallization. The addition products easily undergo chemoselective nitro group reduction and subsequent lactamization with a high synthetic potential. |
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