Organotelluriums. 20. Aminotellurinylation of olefins and its utilization for synthesis of 2-oxazolidinones

Hydroxyamination of Olefins Using Br-N-(CO2Me)2

“…The crude product was purified by column chromatography; 100% DCM; R f = 0.2 (PMA stain); oil; 20 mg; 36% yield (over 3 steps). The compound matched the reported literature data …”

“…The trans oxazolidinones were formed in all cases, as supported by 1 H NMR, NOE, and examination of the reported literature data for compound 4g . The data for the trans stereoisomer of 4g and not the cis stereoisomer of 4g was verified by analysis of the chemical shifts and coupling constants of the methine CH protons of the oxazolidin-2-one ring . As expected, the oxazolidinone 4d gave the syn stereoisomer due to the locked geometry of the indene ring.…”

One-Pot Synthesis of Oxazolidinones and Five-Membered Cyclic Carbonates from Epoxides and Chlorosulfonyl isocyanate: Theoretical Evidence for the Asynchronous Concerted Pathway

“…Products [a] (%) Five-membered cyclic carbonates [b] Oxazolidinones [b] 1 7a 42% 8a [48] 38% 9a [49] 2 7b 48% 8b [50] 45% 9b [51] After having obtained the optimal conditions for the reaction observed, we examined the reactivity of various epoxides to standardize the reaction. Using the optimized conditions, chlorosulfonyl isocyanate was treated with simple epoxides.…”

Catalytic, Enantioselective Syn-Oxyamination of Alkenes

“…Although chalcogens have seen prior use in the dual opening of -iranium ions to effect 1,2-oxyamination of alkenes, this has historically been conducted using stoichiometric amounts of the chalcogen-based reagent. This strategy was first demonstrated in 1988 by Ogura and co-workers using benzenetellurinyl trifluoroacetate to form the telluriranium ion, with opening by the nitrile solvent in a Ritter-type process that ultimately displaces the tellurium through an invertive process that reduces the tellurium reagent (Scheme a) . Shortly thereafter, Tiecco and co-workers demonstrated that stoichiometric amounts of diphenyl diselenide, in the presence of an oxidant, can react with alkenes to form a seleniranium ion that can be opened by a variety of nucleophiles to provide 1,2-amino alcohol scaffolds upon displacement of the selenium (Scheme b) .…”