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pubmed-article:20639467pubmed:issue48lld:pubmed
pubmed-article:20639467pubmed:dateCreated2010-12-1lld:pubmed
pubmed-article:20639467pubmed:abstractTextWe report the development of a multicatalytic, one-pot, asymmetric Michael/Stetter reaction between salicylaldehydes and electron-deficient alkynes. The cascade proceeds via amine-mediated Michael addition followed by an N-heterocyclic carbene-promoted intramolecular Stetter reaction. A variety of salicylaldehydes, doubly activated alkynes, and terminal, electrophilic allenes participate in a one-step or two-step protocol to give a variety of benzofuranone products in moderate to good yields and good to excellent enantioselectivities. The origin of enantioselectivity in the reaction is also explored; E/Z geometry of the reaction intermediate as well as the presence of catalytic amounts of catechol additive are found to influence reaction enantioselectivity.lld:pubmed
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pubmed-article:20639467pubmed:statusPubMed-not-MEDLINElld:pubmed
pubmed-article:20639467pubmed:monthNovlld:pubmed
pubmed-article:20639467pubmed:issn1091-6490lld:pubmed
pubmed-article:20639467pubmed:authorpubmed-author:RovisTomislav...lld:pubmed
pubmed-article:20639467pubmed:authorpubmed-author:LathropStephe...lld:pubmed
pubmed-article:20639467pubmed:authorpubmed-author:FillouxClaire...lld:pubmed
pubmed-article:20639467pubmed:issnTypeElectroniclld:pubmed
pubmed-article:20639467pubmed:day30lld:pubmed
pubmed-article:20639467pubmed:volume107lld:pubmed
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pubmed-article:20639467pubmed:authorsCompleteYlld:pubmed
pubmed-article:20639467pubmed:pagination20666-71lld:pubmed
pubmed-article:20639467pubmed:dateRevised2011-7-28lld:pubmed
pubmed-article:20639467pubmed:year2010lld:pubmed
pubmed-article:20639467pubmed:articleTitleMulticatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.lld:pubmed
pubmed-article:20639467pubmed:affiliationDepartment of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.lld:pubmed
pubmed-article:20639467pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:20639467pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed
pubmed-article:20639467pubmed:publicationTypeResearch Support, N.I.H., Extramurallld:pubmed
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