Document Detail


N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals.
MedLine Citation:
PMID:  22967028     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Fedor Romanov-Michailidis; Céline Besnard; Alexandre Alexakis
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-9-12
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-9-12     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Organic Chemistry, University of Geneva , quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
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