Asymmetric N‑Heterocyclic Carbene (NHC)-Catalyzed Annulation of Modified Enals with Enolizable Aldehydes

N-Heterocyclic carbene (NHC)-catalyzed highly enantioselective lactonization of modified enals with enolizable aldehydes, proceeding via the α,β-unsaturated acylazolium intermediates, is reported. The reaction results in the asymmetric synthesis of synthetically important 4,5-disubstituted dihydropy...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 20; pp. 5202 - 5205
Main Authors Yetra, Santhivardhana Reddy, Kaicharla, Trinadh, Kunte, Sunita S, Gonnade, Rajesh G, Biju, Akkattu T
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.10.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIELS-ALDER REACTIONS
ENANTIOSELECTIVE SYNTHESIS
ACYLOIN CONDENSATIONS
ALPHA,BETA-UNSATURATED ALDEHYDES
ESTERS
ORGANOCATALYSIS
ENAMINES
GENERATION
STEREOSELECTIVE-SYNTHESIS
CATALYZED ANNULATIONS
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Summary:N-Heterocyclic carbene (NHC)-catalyzed highly enantioselective lactonization of modified enals with enolizable aldehydes, proceeding via the α,β-unsaturated acylazolium intermediates, is reported. The reaction results in the asymmetric synthesis of synthetically important 4,5-disubstituted dihydropyranones.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4026155