Dearomatizing Disrotatory Electrocyclic Ring Closure of Lithiated N-Benzoyloxazolidines

Loss of aromaticity ensues when N‐benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis‐tricyclic products epimerize to their more stable trans dia...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2002-03, Vol.41 (6), p.1049-1051
Main Authors: Clayden, Jonathan, Purewal, Savroop, Helliwell, Madeleine, Mantell, Simon J.
Format: Article
Language:English
Subjects:
amides
cyclization
lithiation
pericyclic reaction
stereoselectivity
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Summary:Loss of aromaticity ensues when N‐benzoyl oxazolidines are lithiated and undergo a 6π disrotatory electrocyclization (see scheme). The stereochemistry of the cyclization shows it to be a new example of an electrocyclic ring closure. The cis‐tricyclic products epimerize to their more stable trans diastereoisomers in aqueous acid.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO;2-7