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Relevant academic research and scientific papers

Divergent synthesis of oxazolidines and morpholines: via PhI(OAc)2-mediated difunctionalization of alkenes

Herein we describe the PhI(OAc)2-mediated 1,1- and 1,2-difunctionalization of alkenes with N-tosyl amino alcohols to form oxazolidine and morpholine derivatives. This transformation was realized under mild reaction conditions and allows application to var

Copper-Catalyzed N?F Bond Activation for Uniform Intramolecular C?H Amination Yielding Pyrrolidines and Piperidines

The dual function of the N?F bond as an effective oxidant and subsequent nitrogen source in intramolecular aliphatic C?H functionalization reactions is explored. Copper catalysis is demonstrated to exercise full regio- and chemoselectivity control, which

Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes

We report here the first general method for the geminal diamination and an intermolecular metal-free, geminal aminooxygenation of vinylarenes using hypervalent iodine reagent. A new m-CPBA mediated geminal aminooxygenation is also reported. A novel reagent-switch for the control of migrating group by controlling the two independent geminal addition paths is developed. Deuterium labelling studies and the control studies have provided unambiguous evidences for the phenyl migration and hydride migration in the oxidative geminal difunctionalization process mediated by PhI(OCOCF3)2and m-CPBA, respectively through a semi-pinacol rearrangement.

N-protected 1,2-oxazetidines as a source of electrophilic oxygen: Straightforward access to benzomorpholines and related heterocycles by using a reactive tether

A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance. Open and then close: The O-selective ring-opening reaction of 1,2-oxazetidines with organometallic compounds provides tethered phenol derivatives that can be used to access six-, seven-, and eight-membered heterocyclic systems in only a few steps (see scheme; Ts=tosyl).

Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion

An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang

2,2-difunctionalization of alkenes via Pd(II)-catalyzed aza-Wacker reactions

N-Ts and N-Boc derivatives of 1,2-diamines and 1,2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes. The resulting enamine intermediate generally undergoes cyclization with the second heteroatom to form 1,3-heterocycles. The sequence facilitates the rapid synthesis of saturated oxazolidines, imidazolidines, and their derivatives. Use of N-l-valinol derivatives results in highly diastereoselective reactions, where the net stereochemical outcome diverges between N-Ts and N-Boc.