65645-87-6

Usage

Chemical class

Dioxolanones It belongs to a class of organic compounds that contain a dioxolanone ring.

Chirality

(S)-enantiomer The compound is chiral, meaning it has a non-superimposable mirror image. The (S)-enantiomer is the more common form.

Applications

Pharmaceutical and agrochemical synthesis It is used in the synthesis of various pharmaceuticals and agrochemicals, indicating its importance in the development of new drugs and chemicals.

Specialty chemicals production

It is also used in the production of specialty chemicals, which are high-value, custom-tailored chemicals for specific applications.

Biological activities

Potential anti-inflammatory and anti-cancer properties The compound has been studied for its potential therapeutic effects, although further research is needed to fully understand its biological activities.

Chemical structure

Unique and valuable Its unique chemical structure and reactivity make it a valuable building block in organic synthesis.

Reactivity

Potential applications in drug discovery and development Due to its reactivity and unique structure, the compound can be used in the development of new drugs and pharmaceuticals.

Further research

Ongoing studies More research is needed to fully understand the biological activities and potential applications of 1,3-Dioxolan-4-one, 2,2-dimethyl-5-phenyl-, (S)- in various fields.

Upstream product

• 17199-29-0 (S)-Mandelic acid 
• 67-64-1 acetone 
• 6337-34-4 2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 6337-34-4 2,2-dimethyl-5-phenyl-1,3-dioxolan-4-one 
• 156517-44-1 (5S)-2,2-dimethyl-4-methylene-5-phenyl-1,3-dioxolane 
• 4358-86-5 (S)-mandelamide 
• 15101-68-5 1-phenyl-3-(3-(methoxy)phenyl)propan-1-one 
• 153609-00-8 (4S,5S)-2,2-dimethyl-4-(hydroxymethyl)-5-phenyl-1,3-dioxolane 
• 155749-26-1 [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 266329-43-5 (4S,5S)-2,2-Dimethyl-5-phenyl-[1,3]dioxolane-4-carbonitrile 

Relevant academic research and scientific papers

Enantioselective synthesis of allenes by catalytic traceless petasis reactions

Allenes are useful functional groups in synthesis as a result of their inherent chemical properties and established reactivity patterns. One property of chemical bonding renders 1,3-substituted allenes chiral, making them attractive targets for asymmetric synthesis. While there are many enantioselective methods to synthesize chiral allenes from chiral starting materials, fewer methods exist to directly synthesize enantioenriched chiral allenes from achiral precursors. We report here an asymmetric boronate addition to sulfonyl hydrazones catalyzed by chiral biphenols to access enantioenriched allenes in a traceless Petasis reaction. The resulting Mannich product from nucleophilic addition eliminates sulfinic acid, yielding a propargylic diazene that performs an alkyne walk to afford the allene. Two enantioselective approaches have been developed; alkynyl boronates add to glycolaldehyde imine to afford allylic hydroxyl allenes, and allyl boronates add to alkynyl imines to form 1,3-alkenyl allenes. In both cases, the products are obtained in high yields and enantioselectivities.

A Four-Component Reaction for the Synthesis of Dioxadiazaborocines

A four-component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α-hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines). In this remarkable process, one boronic acid reacts as a carbon nucleophile and the other as a boron electrophile to provide enantio- and diastereomerically pure heterocyclic boronates with multiple stereocenters in high yields.

1,1′-Binaphthylazepine-based ligands for asymmetric catalysis. Part 1: Preparation and characterization of some new aminoalcohols and diamines

Starting from (S)-1,1′-binaphthol, a series of ten novel enantiopure 1,1′-binaphthylazepine-based aminoalcohols and diamines 1a-1j were efficiently prepared and fully characterized. These derivatives, having either only an atropisomeric bridged-binaphthyl backbone or an additional stereogenic carbon center, can be interesting ligands for asymmetric catalysis.

Diastereoselective synthesis of protected 2,3-dihydroxynitriles from 2- hydroxy acids

The DIBAL-H reduction of dioxolanones 2 prepared from 2-hydroxy acids followed by addition of acetone cyanohydrin affords the syn 2,3- dihydroxynitriles in high enantiomerical purities.

Controlled racemization and asymmetric transformation of α-substituted carboxylic acids in the melt

The racemization and asymmetric transformation of a series of α- substituted carboxylic acids, viz. mandelic acid, hydratropic acid, ibuprofen and naproxen, were studied. Several racemization methods for mandelic acid were studied and it was found that base-catalyzed racemization in aprotic polar solvents was the most efficient method. Moreover, a fast and mild base- catalyzed racemization reaction in the melt was developed. DBN turned out to be a very efficient racemizing base for the substrates studied. Combination of the base-catalyzed racemization in the melt with known resolution processes resulted in crystallization-induced asymmetric transformations. Treating racemic ibuprofen or hydratropic acid with 1.5-2.5 equivalents of enantiopure α-methylbenzylamine and a catalytic amount of DBN resulted in the isolation of enantiomerically enriched ibuprofen or hydratropic acid with ees of up to 75% and almost quantitative yields.

Stereoselective Protonation of Carbanions, 5. Effect of Reaction Conditions on the Enantioselective Protonation of Lactone Enolates

Protonation of the enolates 1Li and 2Li by using standard conditions yields enantioselectivities up to 54 and 50percent ee, respectively, depending on the chiral proton source.These values may change dramatically by the following variations (standard ee's in parenthesis): (i) In Et2O/THF (90:10) (S)-2 with 72percent ee (44percent) is formed with (R)-pantolactone (3) but only 48percent ee (39percent) with (R,R)-tartaric ester 4 (Figure 1). (ii) Lewis acids may produce rac-2 (SnCl2, MgBr2) or definitely increase the enantioselectivity: With lactone 3: 46percent ee (44percent); with ester 4: 48percent ee (39percent); with bissulfonamide 7: 67percent ee (47percent) (Table 1, 2). (iii) Lithium chloride (2-4 equiv.) in THF yields (S)-1 with 68percent ee (47percent) and (S)-2 with 77percent ee (39percent) but only if ester 4 is employed as chiral proton source (Figure 2). (iv) Chiral Lewis bases create (S)-2 with up to 30percent ee on protonation with achiral acids (Table 3, 4). (v) Deuteration of 2Li ranges from 16 to 95percent depending on the nature of the base as well as the deuteron source.The degrees of deuteration and enantioselectivity are not correlated.All results demonstrate the complexity of enantioselective protonation of enolates which still needs empirical optimization. - Key Words: Enantioselectivity / Protonation / Solvent effects / Lewis acids / Lithium salts / Deuteration

Stereoselective Protonation of Carbanions, 4. Enantioselective Protonation of Lactone Enolates

The prochiral lithium enolates derived from the five-membered lactones rac-1 and rac-2 were protonated by 37 OH- and 21 NH-chiral proton sources in THF at -78 deg C.The enantioselectivities, determined directly from the reaction mixture by chiral HPLC, ar

OPTICAL ACTIVITY OF LACTONES AND LACTAMS-I; CONFORMATIONAL DEPENDENCE OF THE CIRCULAR DICHROISM OF 1,3-DIOXOLAN-4-ONES

Several optically active 1,3-dioxolan-4-ones were synthesized from corresponding α-hydroxy acids.The Cotton effect sign of these compounds can be explained by Weigans's sector rules.The existence of an equilibrium between envelope and planar conformations