Enantioselective synthesis of heterocyclic compounds mediated by organoselenium reagents

Abstract

The syntheses of several types of enantiopure or enantiomerically enriched heterocyclic compounds by electrophilic additions, nucleophilic substitutions and radical additions ring closure reactions, promoted by chiral non racemic as well as by achiral organoselenium reagents, are presented and discussed.

Organoselenium Chemistry: Role of Intramolecular Interactions

“…Tiecco and co-workers have established novel Se···S interactions using achiral/chiral sulfur-containing electrophilic selenium reagents for efficient asymmetric syntheses . Spectroscopic and chemical evidence demonstrate that the observed high selectivity of the asymmetric reactions is associated with a nonbonding selenium−sulfur interaction.…”

Kinetic and Mechanistic Studies of Base-Catalyzed Phenylselenoetherification of (Z)- and (E)-Hex-4-en-1-ols

“…The products of these selenenylations are very useful because wide ranges of alkenes and nucleophiles can be employed in these transformations and many different subsequent reactions are possible . The presence of internal nucleophiles leads to cyclization reactions, which have been employed in various syntheses for a long time . Cyclofunctionalizations of alkenols promoted by PhSeX (X = Cl, Br) reagents are advantageous in the preparation of tetrahydrofuran (THF)- and tetrahydropyran-type rings because of the mild conditions and low temperatures required for these reactions, which usually allow high stereoselectivity .…”

Recent advances in selenium promoted or catalyzed electrophilic aminations of alkenes and alkynes

“…Electrophilic selenocyclizations (cyclofunctionalizations) of alkenes containing internal nitrogen nucleophiles are very well documented [1][2][3][4][5][6] and some of these reactions have found interesting applications in the preparation of complex molecules and alkaloids. Representative examples are reported in Scheme 15.…”

“…The access to a diverse array of functionalized compounds is critical in drug discovery projects and also for this reason in the past few decades, operationally simple new methodologies for C-N bond formation have been deeply investigated. In this field, the electrophilic seleno-functionalizations of carboncarbon multiple bonds [1][2][3][4][5][6][7][8] offer interesting opportunities, also in consideration of the growing interest in the pharmacological and toxicological properties of selenium-containing compounds. [8][9][10][11][12][13][14] The reaction of alkenes with commercial selenium electrophiles, such as PhSeCl, PhSeBr or Phenylselenophthalimide (NPSP), has been deeply explored (Scheme 1).…”