Extending the Aminocatalytic HOMO-Raising Activation Strategy: Where Is the Limit?

Increasingly remote stereocenters are being targeted in asymmetric aminocatalysis. Application of the HOMO‐raising activation concept to δ,δ‐disubstituted 2,4‐dienones confirms the powerful potential of the trienamine strategy. A cinchona‐based primary amine catalyst enables the extension of this ac...

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Published inAngewandte Chemie (International ed.) Vol. 51; no. 22; pp. 5290 - 5292
Main Authors Arceo, Elena, Melchiorre, Paolo
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 29.05.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Activation
Amines
asymmetric catalysis
Asymmetry
carbonyl compounds
Catalysts
cycloaddition
Diels-Alder reactions
organocatalysis
Strategy
trienamines
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Summary:Increasingly remote stereocenters are being targeted in asymmetric aminocatalysis. Application of the HOMO‐raising activation concept to δ,δ‐disubstituted 2,4‐dienones confirms the powerful potential of the trienamine strategy. A cinchona‐based primary amine catalyst enables the extension of this activation mode to a highly selective asymmetric Diels–Alder reaction of enones with electron‐deficient dienophiles (see scheme; TFA: trifluoroacetic acid).
Bibliography:ArticleID:ANIE201201347
istex:41EE9003D4CEE88AFF8409C9060F2D366BD0FD3B
ark:/67375/WNG-Q60ZZPLK-5
European Research Council - No. 278541
Institute of Chemical Research of Catalonia (ICIQ) Foundation
Financial support from the Institute of Chemical Research of Catalonia (ICIQ) Foundation and the European Research Council (ERC Starting grant agreement no. 278541-ORGA-NAUT) is gratefully acknowledged.
Financial support from the Institute of Chemical Research of Catalonia (ICIQ) Foundation and the European Research Council (ERC Starting grant agreement no. 278541—ORGA‐NAUT) is gratefully acknowledged.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201347