N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-ε-Lactones

Enantioselectivity through H bonding: An unprecedented [4+3] annulation of enals with o‐quinone methides catalyzed by N‐heterocyclic carbenes (NHCs) to give benzo‐ε‐lactones is described. High to excellent enantioselectivity was achieved by using a chiral triazolium NHC having a free OH group, which...

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Published inAngewandte Chemie International Edition Vol. 52; no. 33; pp. 8607 - 8610
Main Authors Lv, Hui, Jia, Wen-Qiang, Sun, Li-Hui, Ye, Song
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 12.08.2013
WILEY‐VCH Verlag
Wiley
Subjects
Aldehydes - chemistry
annulation
Benzoquinones - chemistry
Bonding
Carbenes
Catalysis
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
enantioselectivity
Heterocyclic Compounds - chemistry
Indolequinones - chemistry
Lactones - chemical synthesis
Magnetic Resonance Spectroscopy
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
N-heterocyclic carbene
Organic chemistry
organocatalysis
Physical Sciences
Science & Technology
Stereoisomerism
Synthesis
synthetic methods
enantioselectivity
N-heterocyclic carbene
INTERMOLECULAR STETTER REACTIONS
DIELS-ALDER REACTIONS
ALPHA,BETA-UNSATURATED ALDEHYDES
BAEYER-VILLIGER OXIDATION
EFFICIENT SYNTHESIS
ENOLATE EQUIVALENTS
GAMMA-BUTYROLACTONES
organocatalysis
annulation
COOPERATIVE CATALYSIS
HOMOENOLATE ADDITIONS
STEREOSELECTIVE-SYNTHESIS
synthetic methods
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Summary:Enantioselectivity through H bonding: An unprecedented [4+3] annulation of enals with o‐quinone methides catalyzed by N‐heterocyclic carbenes (NHCs) to give benzo‐ε‐lactones is described. High to excellent enantioselectivity was achieved by using a chiral triazolium NHC having a free OH group, which participates in a hydrogen‐bonding interaction with the substrate.
Bibliography:ark:/67375/WNG-H8NFVL7H-D
Chinese Academy of Sciences
Financial support from the Ministry of Science and Technology of China (2011CB808600), National Natural Science Foundation of China (No. 21072195, 20932008), and the Chinese Academy of Sciences is gratefully acknowledged.
Ministry of Science and Technology of China - No. 2011CB808600
National Natural Science Foundation of China - No. 21072195; No. 20932008
ArticleID:ANIE201303903
istex:18F37A0605BD255C5C641A52ECBBADF215CB6A5A
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201303903