Desymmetric ring-opening of meso-epoxides with anilines: a simple way to chiral β-amino alcohols

Chiral β-amino alcohols were afforded by desymmetric ring-opening of meso-epoxides with anilines catalyzed by chiral Yb triflate complex in up to 80.1% ee.     

Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides

Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.     

Facile access to β-hydroxyl ketones via a cobalt-catalyzed ring-opening/hydroxylation cascade of cyclopropanols

A cobalt-catalyzed ring-opening/hydroxylation cascade of highly strained cyclopropanols has been developed for the first time. The reaction was conducted under open-air atmosphere to afford a broad series of structurally diverse β-hydroxy ketones in moderate to good yields with high regioselectivity. The protocol features mild reaction conditions, simple operation, high-functional-group tolerance, facile scalability, and heterocycle compatibility.     

The facile insertion of β-keto sulfones to arynes: The direct preparation of polysubstituted ortho-keto benzyl sulfones

One novel carbon-carbon bond insertion reaction of arynes has been developed. By this reaction β-keto sulfones can insert the triple bond of arynes to prepare polysubstituted ortho-keto benzyl sulfones.     

Iodine-mediated regioselective hydroxyselenenylation of alkenes:Facile access to β-hydroxy selenides

In the presence of molecular iodine, the reaction of alkenes with diselenides proceeds efficiently under mild reaction conditions in MeCN/H₂O, which affording β-hydroxy selenides with high regioselectivity and in good to excellent yields.     

Synthesis of diverse β-(nitrooxy)-substituted amines by regioselective ring-opening of aziridines under neat conditions

An efficient and regioselective method was developed for the synthesis of β-(nitrooxy)-substituted amine derivatives by ring-opening of different aziridines with Zn(NO₃)₂·6H₂O without using additives or catalyst. A library of β-(nitrooxy)-substituted amine derivatives having a variety of substituents has been synthesized. Excellent regioselectivity, high yields, clean reaction, ease of product isolation, easily accessible reactants, and solvent-free as well as environment friendly reaction conditions are the notable advantages of the present methodology. The nitrooxy derivative was successfully transformed into hydroxy derivative by simple reduction. Gram-scale synthesis demonstrates the potential applications of the present method.     

Synthesis of β-triazolyl sulfones via the reaction of vinyl sulfones with 1,2,4-triazoles under basic conditions

Russian Chemical Bulletin - A method was developed for the synthesis of β-triazolyl sulfones from vinylsulfones and 1,2,4-triazoles in the presence of sodium triazolide taken as the base. The...     

The facile insertion of β-keto sulfones to arynes： The direct preparation of polysubstituted ortho-keto benzyl sulfones

One novel carbon-carbon bond insertion reaction of arynes has been developed. By this reaction β-keto sulfones can insert the triple bond of arynes to prepare polysubstituted ortho-keto benzyl sulfones.     

Aerobic oxysulfonylation of alkynes in aqueous media: highly selective access to β-keto sulfones

The first application of inexpensive commercially available sulfinate salts to produce β-keto sulfones directly from alkynes via aerobic oxysulfonylation has been developed. It is a highly selective (undesired Glaser–Hay homo-coupling and ATRA process totally suppressed) general method of functionalization of alkynes on water at room temperature involving FeCl₃/K₂S₂O₈ catalyzed formation of sulfonyl radicals from sulfinate salts.     

Highly enantioselective reduction of β-amino nitroolefins with a simple N-sulfinyl urea as bifunctional catalyst

Simple but effective: A structurally simple N-sulfinyl urea was found to be a highly efficient bifunctional catalyst, which allows for the development of a novel pathway for the construction of chiral β-amino nitroalkanes through enantioselective reduction of β-amino nitroolefins by trichlorosilane. High yields and excellent enantioselectivities were obtained for a broad range of β-arylamino nitroolefin substrates (see scheme).     

Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: a facile and eco-friendly access to allylic alcohols and amines

Very high regioselective 1,2-addition of organolithiums to α,β-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 °C.     

Direct access to β-seleno sulfones at room temperature through selenosulfonylation of alkenes

A new protocol has been developed for the formation of C.Se and C.S bonds by the direct selenosulfonylation of alkenes.This protocol is operationally simplistic, has a wide substrate scope, uses readily available seleno and sulfonyl sources, and is amenable to gram-scale synthesis. This reaction represents a significant addition to the limited number of reactions available for the intermolecular selenide difunctionalization of alkenes and would be useful for the synthesis of sulfur-and selenium-containing molecules.     

Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: a facile access to α-methylene γ-lactams

The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams.     

A novel oxidative ring-opening reaction of isoxazolidines: syntheses of β-amino ketones and β-amino acid esters from secondary amines

A novel oxidative ring-opening reaction of isoxazolidines upon treatment with an electrophile and subsequently with a basegives β-amino ketones and β-amino acid esters highly efficiently.     

Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.     

γ-Chiral β-ketosulfones in asymmetric synthesis: a unified synthetic strategy for enantiopure γ-amino and γ-hydroxy vinyl sulfones

Enantiopure γ-hydroxy and γ-amino vinyl sulfones have been prepared in a short synthetic sequence from the chiral pool derived γ-acetoxy/amino β-ketosulfones.     

NHC-catalyzed efficient synthesis of β′-amino enones via carbonyl umpolung reaction of enals with aziridines

The first example of N-heterocyclic carbene-catalyzed synthesis of β′-amino-α,β-unsaturated ketones via regioselective ring-opening of terminal aziridines with enals is reported. The protocol involves carbonyl umpolung reactivity of enals in which the carbonyl carbon attacks nucleophilically on electrophilic terminal aziridines. No by-product formation, operational simplicity, ambient temperature, good to excellent yields (76-94%), and regioselectivity are the salient features of the present procedure.     

A quick and regioselective access of spirooxindole-oxazoline by reaction of isatin and isocyanoacetate “on water”

A greener, rapid and regioselective “on water” synthesis of spirooxindole-oxazoline by the reaction of isatin and isocyanoacetate at room temperature is described. The developed protocol has the advantage of being atom-economical, eco-friendly, and benign reaction conditions. Broader substrate scope, experimentally simple procedures, and easy purification of products with high yield further make this method attractive. The synthesized compounds have been fully characterized with spectral analysis.     

Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols

An efficient direct asymmetric aldol reaction between hydroxyacetone and β,γ-unsaturated α-keto esters has been successfully developed. In the presence of 9-amino-9-deoxy-epi-cinchonine and trifluoroacetic acid, the direct aldol reaction of O-protected hydroxyacetone proceeded in a highly enantioselective manner, affording the desired adducts containing a chiral tertiary alcohol in high yields and with excellent enantioselectivities. The aldol products obtained are valuable precursors for the synthesis of 2-substituted glycerol derivatives.