One-pot synthesis of vinylisoxazolidines from simple hydroxylamines and conjugated carbonyls

Synthesis of Isoxazolidines from Substituted Vinylnitrones and Conjugated Carbonyls via Visible‐Light Photocatalysis

“…This trend has been observed under thermal and Lewis acid‐promoted conditions and computational efforts have demonstrated a clear preference for endo products [8] . Marouka has found that changes on the steric bulk of the LA promoter are able to control the regioselectivity of the reaction irrespective of the substrate substitution patterns [9] .…”

From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines

“…We could envision a head-to-tail arrangement of substituted enals as a requirement to provide the correct regioselectivity and number of carbons (Scheme a). Our previous efforts have found that vinyl nitrones and α-substituted enals undergo a selective dipolar cycloaddition to form 3,5-endoisoxazolidines ( IX ) as major products (Scheme b) . Therefore, we envision that a sequential dipolar cycloaddition/reductive cleavage would produce a highly substituted five-membered-ring carbacycle (Scheme c).…”

“…Our previous efforts have found that vinyl nitrones and αsubstituted enals undergo a selective dipolar cycloaddition to form 3,5-endoisoxazolidines (IX) as major products (Scheme 1b). 6 Therefore, we envision that a sequential dipolar cycloaddition/reductive cleavage would produce a highly substituted five-membered-ring carbacycle (Scheme 1c). To the best of our knowledge, this is the first report of such an approach.…”

Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

“…The Moura-Letts laboratory is focused on developing novel methods for the synthesis of complex nitrogen-containing heterocycles. 29 Recent efforts towards novel N-transfer reagents allowed the discovery that chloramine T in the presence of metal oxides and tridentate ligands reacts with alkenes to provide aziridines as the major product. Moreover, the combination of high oxidation state metal oxides, tridentate ligands and phenyl hydroxylamines are known to provide metallooxaziridines and in some examples as reactive intermediates for N-transfer reactions.…”