Novel C2-symmetric chiral ligands: enantioselective transformation of cyclic 1,2-diols into 1,2-bis(phenylsulfenyl) and 1,2-bis(phenylselenyl) derivatives

Development of a novel phosphoramidite-selenide ligand for Pd-catalyzed asymmetric allylic substitution

“…In addition, Skarżewski's group used a kind of C 2 -symmetric chiral Se,Se-donating ligand in Pd-catalyzed asymmetric allylic alkylation obtaining products with moderate ee. 8 In 1999, Hiroi and co-workers developed a chiral P,Se-ligand, which afforded the allylic alkylation product with 86% ee and only moderate yield. 9 Recently, an elegant work on the carbohydrate-derived selenoether-phosphite ligand has also been reported by Pàmies and Diéguez.…”

Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

“…Over the past decade, aryl selenocyanates (ArSeCN) have attracted considerable attention since they displayed biological activity [2] and found wide applications in organic synthesis. For example, aryl selenocyanates have appeared as an important organoselenium reagent to construct various organic selenium compounds including monoselenides, [3a–e] diselenides, [3f,g] trifluoromethyl (difluoromethyl) selenides, [3h,i] selenoesters [3j] and selenium‐containing ligands [3k] . In some cases, aryl selenocyanates could serve as a useful bifunctional reagent for the direct cyanoselenenylation of unsaturated C−C bonds [4]…”

Mechanistic Insight into the CO2 Capture by Amidophosphoranes: Interplay of the Ring Strain and the trans Influence Determines the Reactivity of the Frustrated Lewis Pairs

“…( S , S )‐1,2‐Cyclopentanediol 1 , ( S , S )‐1,2‐cyclohexanediol 2 , ( S , S )‐1,2‐cycloheptanediol 3 , ( S , S )‐1,2‐cyclooctanediol 4 , and ( S , S )‐1,2‐dihydroxy‐1,2,3,4‐terahydronaphthalene 5 were selected as the target vicinal diols, and ( R )‐α‐hydroxycyclopentanone 6 , ( R )‐α‐hydroxycyclohexanone 7 , ( R )‐α‐hydroxycycloheptanone 8 , ( R )‐α‐hydroxycyclooctanone 9 , and ( R )‐α‐hydroxytetralone 10 were chosen as the target α‐hydroxy ketones (Scheme ). These compounds are very useful and valuable chiral building blocks and pharmaceutical intermediates,6–12 and the enantioselective oxidations of racemic cyclic vicinal diols are also very challenging.…”