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Dearomatizing Disrotatory Electrocyclic Ring Closure of Lithiated N ‐Benzoyloxazolidines
Author(s) -
Clayden Jonathan,
Purewal Savroop,
Helliwell Madeleine,
Mantell Simon J.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020315)41:6<1049::aid-anie1049>3.0.co;2-7
Subject(s) - conrotatory and disrotatory , closure (psychology) , ring (chemistry) , computer science , chemistry , economics , organic chemistry , market economy
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.