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An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones

The asymmetric desymmetrization of 3-substituted glutaric anhydrides 1 bearing silyl, aryl and alkyl groups with the lithium salt of chiral oxazolidin-2-ones has been studied. The effects of the substituents at the 4- and 5-positions of the oxazolidin-2-ones on the diastereoselectivity of the anhydride opening were studied in detail. A SuperQuat chiral oxazolidin-2-one 2e with 5,5-diaryl substituents showed optimum selectivity.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Related Products of 184346-45-0. In my other articles, you can also check out more blogs about 184346-45-0

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A useful modification of the Evans auxiliary: 4-Isopropyl-5,5- diphenyloxazolidin-2-one

The 4-isopropyl-5,5-diphenyloxazolidinone (1) is readily prepared from (R)- or (S)-valine ester, PhMgBr, and ethyl chlorocarbonate. It has a melting point of ca. 250, a low solubility in most organic solvents, and a C=O group which is sterically protected from nucleophilic attack. Thus, the soluble N-acyl-oxazolidinones (7-16) can be prepared from 1 with BuLi at temperatures around 0instead of – 78(Scheme 3), their Li enolates can be generated with BuLi, rather than with LDA, and deacylation in the final step of the procedure can be achieved with NaOH at ambient temperatures (Scheme 12), with facile recovery of the precipitating auxiliary 1 (filtering, washing, and drying). The following reactions of N-acyl-oxazolidinones from 1 have been investigated: alkylations (Scheme 4), aminomethylations and hydroxymethylations (Scheme 5), aldol additions (Schemes 6 and 7), Michael additions (Schemes 9 and 10), and a (4 + 2) cycloaddition (Scheme 11). The well-known features of reactions following the Evans methodology (yield, diastereoselectivity, dependence on conditions, counter ions, additives etc.) prevail in these transformations. Most products, however, have higher melting points and a much more pronounced crystallization tendency than those derived from conventional oxazolidinones, and can thus be purified by recrystallization, avoiding chromatography (Table 1). The disadvantage of 1 having a higher molecular weight (ca. 150 Da) than the non-phenyl-substituted auxiliary is more than compensated by the ease of its application, especially on large scale. A number of crystal structures of oxazolidinones derived from 1 and a TiCl4 complex of an oxazolidinone are described and discussed in view of the diastereoselective-reaction mechanisms.

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.name: (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one, you can also check out more blogs about184346-45-0

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A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers

(Chemical Equation Presented) A stereoselective halo-etherification of chiral enamides is described here. This work provides an approach to halogen containing cyclic ethers and reveals further mechanistic insights to the chemistry of chiral enamides.

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Conjugate addition of lithiated (S)-4-isopropyl-3-[(methylthio)methyl]-5,5-diphenyloxazolidin-2-one to cinnamoyl derivatives: Preparation of enantiomerically pure 1,4-diols

The Li derivative of (S)-4-isopropyl-3-[(methylthlio)methyl]-5,5-diphenyloxazolidin-2-one (Li-2; synthetically equivalent to a chiral formyl anion) adds to enones and enoates in a 1,4-fashion. Best results are obtained with 1,3-diarylpropenones (chalcones; Scheme2), trityl enones, and 2,6-di(tert-butyl)-4-methoxyphenyl cinnamates (Scheme 3), with yields up to 80% and diastereoselectivities up to and above 99: 1 of the products (5a – f and 8a,b,e) containing three stereogenic centers! X-Ray crystal-structure analysis reveals that the C,C-bond formation occurs preferentially with relative topicity ul (Re/Si; Fig. 2). The MeS group of the 1.4-adducts can be replaced by RO groups in Hg2¡Â-assisted substitutions, with subsequent removal and facile recovery of the chiral auxiliary (Schemes 4-6). 4-Hydroxycarbonyl derivatives (‘homoaldols’) and mono-, di-, and trisubstituted 1,4-diols are, thus, accessible in enantiomerically pure forms (cf. 15, 16, and 18-20).

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 184346-45-0, name is (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one, introducing its new discovery. Safety of (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

Resolution of pentafluorophenyl esters using oxazolidin-2-ones

A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-one. The levels of diastereocontrol were found to be excellent (80-96% de) at ?40% conversion.

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, COA of Formula: C18H19NO2, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 184346-45-0, Name is (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one, molecular formula is C18H19NO2

A synthesis of (S)-alpha-(fluorodiphenylmethyl)alkylamines by HF-pyridine treatment of 4-alkyl-5,5-diphenyl-oxazolidinones

Treatment of enantiomerically pure (S)-4-alkyl-5,5-diphenyl-oxazolidinones, themselves derived from appropriate amino acids, with HF-pyridine (Olah’s reagent) generated a range of (S)-alpha-(fluorodiphenylmethyl)alkylamines. These compounds represent a novel range of fluorinated chiral amines. Copyright (C) 2000 Elsevier Science Ltd.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. COA of Formula: C18H19NO2, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 184346-45-0, in my other articles.

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Recommanded Product: (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 184346-45-0, name is (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one. In an article£¬Which mentioned a new discovery about 184346-45-0

Metallations and reactions with electrophiles of 4-isopropyl-5,5-diphenyloxazolidin-2-one (DIOZ) with N-allyl and N-propargyl substituents: Chiral homoenolate reagents

N-Allyl, N-cinnamyl, and N-(3-trimethylsilyl)propargyl derivatives of 4-isopropyl-5,5-diphenyloxazolidin-2-one (DIOZ) are prepared by lithiation of the parent DIOZ (with BuLi in THF) and reaction with the corresponding bromides (Scheme 1). Lithiation in the same solvent, with deprotonation by BuLi on the allylic or propargylic CH2 group at dry-ice temperature, provides colorful solutions, which are either combined with aldehydes or ketones directly or after addition (with or without warming) of (Me2N)3TiCl or (i-PrO)3TiCl. Conditions have thus been elaborated under which all three types of conjugated lithium compounds react in the gamma-position with respect to the oxazolidinone N-atom: carbamoyl derivatives of enamines and allenyl amines are formed in yields ranging from 60 to 80% and with diastereoselectivities up to 98% (Schemes 2-5). The C= C bond of the N-hydroxyalkenyl groups has (Z)-configuration (products 5 and 8), the allene chirality axis has (M)-configuration (products 9), and the addition to aldehydes and unsymmetrical ketones has taken place preferentially from the Si face. A mechanistic model is proposed that is compatible with the stereochemical outcome (assuming kinetic control and disregarding the presence of Li and Ti species in the reaction mixture; cf. L, M in Fig. 4). Hydrolysis of the enamine derivatives leads to lactols, oxidizable to gamma-lactones, with recovery of the crystalline oxazolidinone, as demonstrated in three cases (Scheme 6). Thus, the application of chiral oxazolidinone auxiliaries (cf. Figs. 1 and 2) has been extended to the overall enantioselective preparation of homoaldols.

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Facile formation of N-acyl-oxazolidinone derivatives using acid fluorides

A mild method is presented for the formation of N-acylated oxazolidinones that employs acid fluorides and mild bases, such as iPr 2NEt and NEt3. Optimized reaction conditions for two types of substrates have been developed utilizing either the oxazolidinone itself or the corresponding in situ generated O-silyloxazolidinones resulting in the formation of the desired N-acylated products in high yields of up to 98%.

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