Role of a Protected Vicinal Diol Controller in Intramolecular Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

Article abstract of DOI:10.1021/jo00095a008

Intramolecular cycloaddition reactions of C5-chain acyclic alkenyl nitrones such as N-<(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene>benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo<3.2.0> framework) with very high diastereomeric excess.These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.