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Diastereoselective Bromocyclization of O‑Allyl‑N‑tosyl-hydroxylamines

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posted on 2013-03-15, 00:00 authored by Boris Egart, Dieter Lentz, Constantin Czekelius
The intramolecular bromoamination of O-allyl-N-tosyl-hydroxylamines results in the formation of isoxazolidines via selective 5-endo-tet cyclization. This process occurs trans-selectively in high yield and diastereoselectivity. The obtained bromo-isoxazolidines provide access to other useful building blocks, such as 2-azido-aminoalcohols, diaminoalcohols, and aziridines.

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