Synthesis of Chiral Selenazolines from N-Acyloxazolidinones via a Selenative Rearrangement of Chiral Cyclic Skeletons

Abstract

A synthetic route to chiral selenazolines from readily available N-acyloxazolidinones via a selenative rearrangement of a chiral cyclic skeleton is reported. The reaction proceeds in the presence of elemental selenium, a hydrochlorosilane, and an amine. Although the stability of the obtained selenazoline products is relatively low, a wide range of selenazolines was successfully prepared.

A base-free copper-assisted synthesis of C2-symmetric spirotelluranes and biaryls based on divergent stoichiometry of Na2Te

“…In the past few decades, organochalcogen (S, Se, and Te) chemistry has received significant attention amongst chemists due to its use in the field of synthetic organic chemistry, 1–3 dyes, 4 and biology. 5 Organotelluriums have been studied for years and show promising activities for the decomposition of peroxides, 6 as radical chain braking antioxidants, 7 and as antitumor 8 and antileishmanial 9 agents (Chart 1).…”

Exo-trig selenocyclization of secondary allylic carboxamides using Woollins’ reagent: en route to 2,5-disubstituted selenazolines

“…2a,b Moreover, the synthetic routes that are available suffer from distinct limitations such as burdensome multiple reaction steps, the involvement of multiple substrates, long reaction times, etc. 7,8 The reported method can address all of these limitations. A single reagent, i.e., WR, has been utilized for the singlestep synthesis of substituted selenazolines, assisted by microwave heating which accelerates the reaction rate for completion in 45 min.…”

“…The reason for this could be the oxophilic nature of the phosphorus in WR that d,4a,c,9 and (b) the synthetic feasibility of substituted selenazolines. 7,8 Fig. 3 Overview of the present work.…”

“…Fig.2Previous reports on (a) the chemical reactivity of Woollins' reagent3b,d,4a,c,9 and (b) the synthetic feasibility of substituted selenazolines 7,…”

Oxidative Aminoarylselenation of Maleimides via Copper-Catalyzed Four-Component Cross-Coupling

“…As part of our design, we speculated that enamides and arylselenocopper species could be generated on the basis of distinct mechanisms of copper-catalyzed reactions in a one-pot manner and then two competent intermediates undergo selective cross-coupling to afford the corresponding product. However, a formidable challenge in this approach is to overcome a number of competitive reactions, including copper-catalyzed Ullmann amination, seleno-Michael addition, selenation of maleimides, and homocoupling (Scheme C). As a result, this transformation establishes a useful approach to access arylselenoamination of maleimides via one C–N bond and double C–Se bond formation processes.…”