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.
|Number of pages||3|
|Journal||Angewandte Chemie - International Edition|
|Publication status||Published - 15 Mar 2002|
- Pericyclic reaction