Exploration and Development of Nitrone Chemistry
Osamu Tamura
Abstract
Nitrones are widely used as 1,3-dipoles in organic synthesis, but control of their reactions is not always easy. This review outlines our efforts to make the reactions of nitrones more predictable and easier to use. These efforts can be categorized into (1) 1,3-nucleophilic addition reaction of ketene silyl acetals to nitrones, (2) geometry-controlled cycloaddition of C-alkoxycarbonyl nitrones, (3) stereo-controlled cycloaddition using double asymmetric induction, and (4) generation of nitrones by N-selective modification of oximes.
Topics & Concepts
NitroneKeteneCycloadditionSilylationChemistryCombinatorial chemistryOrganic synthesisNucleophilic additionNucleophileOrganic chemistryCatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsOrganic Chemistry Cycloaddition Reactions