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Resolution of a racemic 1,2-diol using triphenylmethyl protection of the primary hydroxyl group and Mucor miehei lipase (Lipozyme) for the kinetic resolution

The triphenylmethyl group gives very simple access to the 1-protection of 1,2-diol as exemplified by racemic propane-1,2-diol. This group has, however, been shown to be incompatible with lipases commonly used for the resolution of alcohols. This turned out to be the case for Pseudomonas cepacia lipase, which we have used in our earlier work. Lipozyme, a Mucor miehei lipase, best known for 1,3-selectivity with glycerol is, however, shown to catalyze transacetylation onto the secondary hydroxyl group next to a triphenylmethoxy group. The transacetylation is completely enantioselective for the (R)-enantiomer giving a very simple method for the resolution of this type of 1,2-diol enantiomer.

Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Chemoselective transfer hydrogenation of alpha,beta-unsaturated carbonyls using palladium immobilized ionic liquid catalyst

This work reports a simple and highly efficient protocol for chemoselective transfer hydrogenation of alpha,beta-unsaturated carbonyls using immobilized palladium metal-containing ionic liquid as a versatile heterogeneous catalyst with an excellent conversion and chemoselectivity (up to 100 %). The influence of various reaction parameters such as the effect of hydrogen donor, solvent, temperature, and time were studied. The catalyst was recycled for four consecutive cycles without significant loss in the catalytic activity. The developed protocol is more advantageous due to the use of HCOONH4 as a hydrogen source, mild reaction conditions, and simple workup procedure and applicable for a wide range of substrates.

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Expedient synthesis of (-)-(1S, 2R)-allonorcoronamic acid

The title amino acid was synthesized in enantiomerically pure form, starting from (S)-(+)-1,2-propanediol 2 in three steps, by condensation of cyclic sulfate 3 with methyl benzylideneglycinate.

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Gem-Dimethyl-cyclo-propanation of dibenzyl-ideneacetone using triisopropyl sulfoxonium tetra-fluoro-borate

The reaction between dibenzyl-ideneacetone (dba) and tri-isopropyl sulfoxonium tetra-fluoro-borate has been reinvestigated. The stereochemistry of the major diasteromeric bis-(gem-dimethyl-cyclo-propane) adduct has now been assigned as [(1RS,3RS)-2,2-dimethyl-3-phenyl-cyclo-prop-yl][(1SR,3SR)-2,2- dimethyl-3-phenyl-cyclo-prop-yl]methanone, C23H26O, by X-ray crystallographic studies on a twinned crystal. The asymmetric unit contains two ml-ecules of the adduct, the conformations of which differ in the orientation of the phenyl ring relative to the adjacent cyclo-propanated double bond. The carbonyl groups of each adduct are aligned approximately along the a axis and in opposite directions to each other. The mol-ecules pack to give a sinusoidal pattern along the b axis. This is the first acyclic bis-(dimethyl-cyclo-prop-yl) ketone for which an X-ray crystal structure determination has been reported, and is also the first bis-cyclo-propanated dba analogue. The knowledge that the major diastereomer has the meso structure (and therefore the confirmation that the minor isomer is the racemate) will prove invaluable in future studies to utilize bis-(dimethyl-cyclo-prop-yl) ketones as reagents, in rearrangement processes, and as potential ligands and ligand precursors in organometallic chemistry.

New explortion of (S)-Butane-1,3-diol

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Synthesis, crystal structures, and electrospray ionisation mass spectrometry investigations of ether- And thioether-substituted ferrocenes

A number of ether- and thioether-substituted ferrocenes (1,1?-bis(1,3-dioxane-2-yl)ferrocene 1, 1,1?-bis(5-methyl-1,3- dioxane-2-yl)ferrocene 2, 1,1?-bis(4-methyl-1,3-dioxane-2-yl)ferrocene 3, 1,1?-bis[(R)-(-)-4-methyl-1,3-dioxane-2-yl]ferrocene 4, 1,1?-bis(4,6-dimethyl-1,3-dioxane-2-yl)ferrocene 5, and 1,1?-bis(1,3-dithiane-2-yl)ferrocene 6) were synthesised by direct condensation of 1,1?-diformylferrocene with the corresponding diols or dithiols. The crystal structures of 1, 5a, 5b, and 6 were determined by X-ray diffraction studies. Electrospray ionisation mass spectrometry was used to investigate the binding behaviour of 1 and 6 toward alkali as well as transition metal cations. The dioxane-containing species 1 showed high affinity toward Li+ and Na+, whereas the dithiane derivative 6 bound, as expected, preferentially to Hg2+. The Royal Society of Chemistry 2003.

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Substrate Structure and Solvent Hydrophobicity Control Lipase Catalysis and Enantioselectivity in Organic Media

The lipase from Candida cylindracea catalyzes the enantioselective esterification of 2-hydroxy acids in nearly anhydrous organic solvents with primary alcohols as nucleophiles. The nature of the 2-hydroxy acid and organic reaction medium affects the efficiency of catalysis and the enantioselectivity. Straight-chain 2-hydroxy acids are highly reactive and give nearly 100% enantioselectivities in esterification reactions with 1-butanol. Slight branching with a methyl group adjacent to the 2-hydroxy moiety in toluene causes a substantial loss (up to 200-fold) in the lipase’s catalytic efficiency with a concomitant loss in enantioselectivity. Losses in catalytic efficiency and enantioselectivity are also observed when the lipase is employed in hydrophilic organic media such as dioxane or tetrahydrofuran as compared to hydrophobic solvents such as toluene. With straight-chain substrates, the lipase is over 100-fold more active in toluene than in tetrahydrofuran or dioxane, while optimal enantioselectivity is observed in toluene. The loss in enantioselectivity in hydrophilic solvents is mainly due to a drop in the catalytic efficiencies of the S isomers, as the R isomers’ catalytic efficiencies remain largely unchanged. In highly apolar solvents, such as cyclohexane, enantioselective relaxation occurs due to an increase in the reactivity of the R isomers relative to that of their S counterparts. These findings enabled a rational selection of substrates and solvents for a two-step, chemoenzymatic synthesis of optically active 1,2-diols to be carried out, the first step being the aforementioned enantioselective esterification of 2-hydroxy acids followed by reduction with LiAl(OCH3)3H to give the optically active 1,2-diol. Diols such as (S)-(+)-1,2-propanediol, (S)-(-)-1,2-butanediol, (S)-(-)-1,2-hexanediol, and (S)-(-)-4-methyl-1,2-pentanediol were produced in high optical purities (at least 98% enantiomeric excess (ee)).

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Stereoselective functionalisation of SuperQuat enamides: asymmetric synthesis of homochiral 1,2-diols and alpha-benzyloxy carbonyl compounds

Homochiral (E)- and (Z)-enamides derived from SuperQuat (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane. Subsequent epoxide opening with meta-chlorobenzoic acid proceeds via a stereoselective SN1-type process, with retention of configuration, to give the corresponding 1?-m-chlorobenzoyl-2?-hydroxy derivatives. Treatment of the SuperQuat enamides with mCPBA effects this two-step transformation in one pot. Reductive cleavage of the isolated 1?-m-chlorobenzoyl-2?-hydroxy derivatives (?96% de) generates homochiral 1,2-diols in ?96% ee. Alternatively, regioselective lithiation of the enamide at C(1?) with tBuLi followed by reaction with an aromatic aldehyde and in situ O-benzylation generates a 1?-(benzyloxy-aryl-methyl) substituted enamide with high diastereoselectivity. Subsequent oxidative cleavage of the enamide C{double bond, long}C bond with NaIO4/RuCl3 followed by methanolysis of the resultant N-acyl fragment furnishes an O-benzyl protected alpha-hydroxy methyl ester in high ee.

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Low-valent titanium induced simultaneous reduction of nitro group and S-S bond in nitrodisulfides: A novel method for the synthesis of benzothiazoline, benzothiazoles and 2,3-dihydro-1,5-benzothiazepines

The simultaneous reduction of nitro group and S-S bond in nitrodisulfides by TiCl4/Sm system leds to the active intermediates 2, which were ‘living’ double-anions (nitride anions and sulfide anions) in situ. These new anion species reacted smoothly with aldehydes or ketones, acid chlorides or acid anhydrides and alpha,beta-unsaturated ketones respectively to afford the desired benzothiazolines, benzothiazoles and 2,3-dihydro-1,5-benzothiazepines in good yields under mild and neutral conditions.

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Tris(cyclopentadienyl)lanthanide Complexes as Catalysts for Hydroboration Reaction toward Aldehydes and Ketones

It was found that homoleptic cyclopentadienyl lanthanide complexes Cp3Ln (Ln = Y (1), Yb (2), Sm (3), Nd (4), La (5), Cp = cyclopentadienyl) can be employed as excellent catalysts for the hydroboration of various aldehydes and ketones toward pinacolborane. These robust lanthanide catalysts exhibited high reactivity with low catalyst loadings (0.01-1 mol %) under mild conditions and good functional group tolerability. These complexes also demonstrated uniquely carbonyl-selective hydroboration in the presence of alkenes and alkynes.

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Novel photo-polymerizable chiral hydrogen-bonded self-assembled complexes: Preparation, characterization and the utilization as a thermal switching reflective color film

In this study, novel photopolymerizable chiral hydrogen-bonded self-assembled complexes (PCHSCs) were fabricated, which were derived from photopolymerizable 4-(6-acryloyloxyhexyloxy) benzoic acid (AHBA, proton donor) and chiral pyridine derivatives (proton acceptor). Their structures were characterized by fourier transform infrared (FT-IR) and the proton nuclear magnetic resonance (1H-NMR) spectoscopy. The thermal stability, phase behaviors and helical twisted power (HTP) characteristics of the PCHSC were investigated by measuring the variable-temperature FT-IR spectrum, differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and the Cano wedge. The results demonstrate that all the PCHSCs have good thermal stability within a temperature range, and the pitch length of all the cells containing the PCHSCs increases with increasing temperature, which is due to the fact that the HTP values of all the PCHSCs decrease with an increase of temperature. What’s more, the introduction of AHBA leads to chiral enhancement of the PCHSCs. Based on the above results, a polymer stabilized cholesteric liquid crystals (PSCLCs) composite with the above PCHSCs was prepared and the thermal-optical characteristics of the PSCLCs film were investigated. The results confirm that the reflective wavelength of the PSCLCs film before and after irradiation can be thermally switched to reflect green and red color from the initial state reflecting a blue/green color with the temperature increasing from 30 C to 75 C. On the basis of this mechanism, the novel material in this study can be used as optical/photonic paper, optical sensors and LCs displays, etc.