Photochemical type II reaction of atropchiral benzoylformamides to point chiral oxazolidin-4-ones. Axial chiral memory leading to enantiomeric resolution of photoproducts

Atropisomeric benzoylformamides 1 undergo Type II reaction leading to cis-2 and trans-2 oxazolidin-4-one photoproducts. The N-C(Aryl) chiral axis is maintained during the course of the phototransformation in spite the reaction proceeding through a near planar intermediate(s). As the rotational barri...

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Published inChemical communications (Cambridge, England) Vol. 46; no. 26; pp. 4791 - 4793
Main Authors Jesuraj, Josepha L., Sivaguru, J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.07.2010
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALPHA-OXOAMIDES
LACTAM
PHOTOCYCLIZATION
AUXILIARY
AMIDES
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Summary:Atropisomeric benzoylformamides 1 undergo Type II reaction leading to cis-2 and trans-2 oxazolidin-4-one photoproducts. The N-C(Aryl) chiral axis is maintained during the course of the phototransformation in spite the reaction proceeding through a near planar intermediate(s). As the rotational barrier of the N-C(Aryl) chiral axis in the cis-2 and trans-2 photoproducts is lowered when compared with the reactant 1, the isolated optically pure trans-2 isomer is converted to the ent-cis-2 isomer without affecting the C-5 stereogenic center, resulting in resolution of the cis-2 enantiomers.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c0cc00470g