Light-induced stereospecific intramolecular [2+2]-cycloaddition of atropisomeric 3,4-dihydro-2-pyridones

Atropisomeric 3,4-dihydro-2-pyridones undergo stereospecific [2+2]-photocycloaddition in solution with high stereoselectivity (ee > 98% and de > 96%) in the product. The chiral transfer during phototransformation was rationalized based on the stability/reactivity of the biradical.

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 49; no. 39; pp. 4346 - 4348
Main Authors Kumarasamy, Elango, Sivaguru, J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2013
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stability
Stereoselectivity
STEREOSELECTIVITY
PHOTOCHEMICAL-REACTIONS
CHIRALITY
AMIDES
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Summary:Atropisomeric 3,4-dihydro-2-pyridones undergo stereospecific [2+2]-photocycloaddition in solution with high stereoselectivity (ee > 98% and de > 96%) in the product. The chiral transfer during phototransformation was rationalized based on the stability/reactivity of the biradical.
Bibliography:National Science Foundation
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc37123e