TCI B6377, N-benzylhydroxylamine (CAS 622-30-0), is a nitrogen–oxygen reagent widely used to generate nitrones by condensation with aldehydes and ketones. The resulting nitrones act as 1,3-dipoles in cycloaddition reactions, providing efficient access to isoxazolidine rings with useful regio- and stereocontrol. Reductive ring opening of those isoxazolidines then delivers valuable 1,3-amino alcohol motifs, while the benzyl group can be removed by hydrogenolysis to unmask the nitrogen. AMI Scientific supplies this TCI reagent in a 1 g pack size; as with hydroxylamine derivatives generally, cool storage in a tightly closed container is recommended.
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- Merino et al. (1999). ChemInform Abstract: Synthesis of Isoxazolidin‐5‐ones via Stereocontrolled Michael Additions of Benzylhydroxylamine to L‐Serine Derived α,β‐Unsaturated Esters.. ChemInform doi:10.1002/chin.199917133
- BONACCORSI et al. (1997). ChemInform Abstract: A Convenient Large Scale Synthesis of O‐Benzylhydroxylamine.. ChemInform doi:10.1002/chin.199728070
- Bonaccorsi et al. (1997). A Convenient Large Scale Synthesis of O-Benzylhydroxylamine. Synthetic Communications doi:10.1080/00397919708003349
References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.
