Mukaiyama-Michael reactions with acrolein and methacrolein: a catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins |
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Authors: | Kemppainen Eeva K Sahoo Gokarneswar Valkonen Arto Pihko Petri M |
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Institution: | Department of Chemistry and Nanoscience Center, University of Jyv?skyl?, POB 35, FIN-40014 JYU, Finland. |
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Abstract: | Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described. |
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