| N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals. | |
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MedLine Citation:
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PMID: 22967028 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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In this paper, the first stereoselective annulation reaction between α-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference. |
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Authors:
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Fedor Romanov-Michailidis; Céline Besnard; Alexandre Alexakis |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-9-12 |
Journal Detail:
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Title: Organic letters Volume: - ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2012 Sep |
Date Detail:
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Created Date: 2012-9-12 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Organic Chemistry, University of Geneva , quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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