title: Mukaiyama-Michael reactions with acrolein and methacrolein: a catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins.
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.
authors.affiliation: Department of Chemistry and Nanoscience Center, University of Jyväskylä, POB 35, FIN-40014 JYU, Finland.
authors.forename: Eeva K
authors.initials: EK
authors.lastname: Kemppainen
authors.forename: Gokarneswar
authors.initials: G
authors.lastname: Sahoo
authors.forename: Arto
authors.initials: A
authors.lastname: Valkonen
authors.forename: Petri M
authors.initials: PM
authors.lastname: Pihko
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry*; D002384:Catalysis; D008387:Marine Toxins / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D008387:Marine Toxins; D011714:Pyrans; D000171:Acrolein; C039175:methacrylaldehyde