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Electronic tuning of the PNNP ligand for the asymmetric cyclopropanation of olefins catalysed by [RuCl(PNNP)]+

Cationic ruthenium complexes of the type [RuCl(L)(PNNP)]+ (L=OEt2, OH2), where PNNP is the CF3-subsituted PNNP ligand N,N?-bis[o-(bis(4-trifluoromethylphenyl)phosphino)benzylidene]- (1S,2S)-diaminocyclohexane 1b, catalyse the asymmetric cyclopropanation of styrene, alpha-Me-styrene, and 1-octene with ethyl diazoacetate. These complexes are more active and give higher cis- and enantioselectivities than their analogues containing the unsubstituted ligand 1a. Thus, [RuCl(OEt2)(1b)]PF6 cyclopropanates alpha-Me-styrene with 85% cis selectivity and 86% ee in 94% isolated yield.

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Cytotoxicity and Structural Analyses of 2,2?-Bipyridine-, 4,4?-Dimethyl-2,2?-bipyridine- and 2-(2?-Pyridyl)quinoxalineplatinum(II) Complexes

Platinum anticancer complexes incorporating 2,2?-bipyridine (bpy), 4,4?-dimethyl-2,2?-bipyridine (44Me2bpy) or 2-(2?-pyridyl)quinoxaline (2pq) as polyaromatic ligands and the S,S or R,R isomer of 1,2-diaminocyclohexane as ancillary ligands in the form [Pt(PL)(AL)]2+ have been synthesised and characterised. X-ray diffraction was used to elucidate the structure and stacking behaviour of the complexes, revealing interesting properties that may impact their biological activity. Pulsed gradient spin-echo NMR experiments elucidated the aggregation behaviour of these complexes in solution. The cytotoxicity of each complex was assessed against the L1210 murine leukaemia, HT29 human colon carcinoma and U87 human glioblastoma cell lines and compared to other complexes within this class. The complexes incorporating 44Me2bpy were found to be the most potent at inhibiting cell growth with IC50 values for the S,S isomer (0.13-0.5 muM) less than that for cisplatin (0.36-11 muM), oxaliplatin (0.9-1.8 muM) or carboplatin (>50 muM). Most complexes were found to be very effective against HT29 colon carcinoma cells.

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Manganese-salen catalyzed oxidative benzylic chlorination

Abstract: Metalloporphyrins are well-known to serve as the model for mimicking reactivities exhibited by cytochrome P450 hydroxylase. Recent developments on selective C?H halogenation using Mn-porphyrins provided the way for understanding the reactivity as well as mechanism of different halogenase enzymes. In this report, we demonstrated a method for benzylic C?H chlorination using easily prepared Mn(salen) complex as the catalyst, which shows a complementary reactivity of Mn-porphyrins. Here, NaOCl has been used as a chlorinating source as well as the oxidant. Efforts towards understanding the mechanism suggested the formation of the high-valent Mn(V)=O species which is believed to be the key intermediate to conduct this transformation. Graphical abstract: SYNOPSIS Mn(salen)-catalyzed selective benzylic chlorination protocol has been developed using aqueous NaOCl solution. Reactions proceeded efficiently at room temperature and displayed good functional group tolerance. The mechanistic investigation demonstrated that Mn (V) = O species is likely to be the key intermediate which is responsible to generate benzylic radical. EPR and ESI-MS studies confirmed the in situ formation of Mn(IV)-species.[Figure not available: see fulltext.].

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Highly enantioselective Diels Alder reactions of Danishefsky type dienes with electron-deficient alkenes catalyzed by Yb(III)-BINAMIDE complexes

1-Methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky-s diene) is recognized as a synthetically useful diene due to its high reactivity in the Diels-Alder reaction with electron-deficient alkenes to give oxygen-functionalyzed cyclohexenes and substituted cyclohexenones, which are important building blocks for the total synthesis of natural products. However, the development of catalytic enantioselective versions of Diels-Alder reactions using Danishefsky type dienes with electron-deficient alkenes has been difficult because of the instability of the dienes under Lewis acidic conditions. Only highly reactive C=O and C=N double bonds are employed in a hetero-Diels-Alder reaction which proceeds under catalysis of chiral Lewis acids. We have developed a new chiral ligand, BINAMIDE, which is easily prepared from 1,1?-binaphtyl-2,2?-diamine by acylation. The highly diastereo- and enantioselective Diels-Alder reaction of Danishefsky type dienes with electron-deficient alkenes in the presence of an Yb(III)-BINAMIDE complex has been developed. The reaction proceeded in an exoselective mode and gave chiral highly functionalized cyclohexene derivatives in good yields. Copyright

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Method of producing optically active aziridine compounds and amine compounds

An optically active aziridine compound or amine compound is produced by using a specified Ru(salen)(CO) complex as a catalyst, and subjecting a specified olefin to an asymmetric aziridination or amination with a specified arylsulfonyl azide compound.

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Highly enantioselective fluorescent recognition of mandelic acid derivatives by chiral salen macrocycles

Calixarene-like chiral salen macrocycles can be used for the enantioselective fluorescent recognition of mandelic acid derivatives. It was observed that one enantiomer of mandelic acid causes a 28-fold increase in the fluorescence intensity of a chiral salen macrocycle, whereas the other enantiomer causes only a 14-fold fluorescence enhancement. This highly enantioselective fluorescent response makes chiral salen macrocycles useful for the enantioselective fluorescent recognition of some mandelic acid derivatives.

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Enantioselective Michael addition of alpha,alpha-disubstituted aldehydes to maleimides organocatalyzed by chiral primary amine-guanidines

New primary amine-guanidines derived from the monoguanylation of (1S,2S)- and (1R,2R)-cyclohexane-1,2-diamine have been prepared and used as chiral organocatalysts for the enantioselective conjugate addition of alpha,alpha-disubstituted aldehydes to maleimides. The corresponding Michael adducts bearing a new stereocenter were generally obtained in high or quantitative yields and with good enantioselectivities (up to 93% ee).

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Optically active dioxatetraazamacrocycles: Chemoenzymatic syntheses and applications in chiral anion recognition

Two new C2 and D2 symmetrical dioxatetraaza 18-membered macrocycles [(R,R)-1 and (S,S,S,S)-2] are efficiently synthesized in enantiomerically pure forms by a chemoenzymatic method starting from (¡À)-trans-cyclohexane-1,2-diamine. The protonation constants and the binding constants with different chiral dicarboxylates are determined in aqueous solution by means of pH-metric titrations. The triprotonated form of (S,S,S,S)-2 shows moderate enantioselectivity with malate and tartrate anions (DeltaDeltaG = 0.62 and 0.66 kcal mol-1, respectively), being the strongest binding observed in both cases with the L enantiomer. Good enantiomeric discrimination is obtained with tetraprotonated (R,R)-1 and N-acetyl aspartate, the complex with the D-enantiomer being 0.92 kcal mol-1 more stable than its diastereomeric counterpart. Despite the lack of enantioselectivity of tri-and tetraprotonated (R,R)-1 for the tartrate anion, a very good diastereopreference for meso-tartrate is found. All these experimental results allow us to propose a model for the host-guest structure based on coulombic interactions and hydrogen bonds.

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Structural Study of Optical Resolution. XVI. The Crystal Structures of a Pair of Diastereomeric Salts of the lel3-Tris(trans-1,2-cyclohexanediamine)nickel(II) Complex with d-Tartrate Dianion

The crystal structures of the diastereomeric salt pair, Lambda-lel3-(d-tart)*3H2O (1) and Lambda-lel3-(d-tart)*5H2O (2) (chxn=trans-1,2-cyclohexanediamine and d-tart=(+)-(R,R)-tartrate dianion), have been determined by a single-crystal X-ray diffraction techniques.Crystal 1 is orthorhombic with the space group P212121, a=10.093(2), b=13.589(4), c=22.011(4) Angstroem, and Z=4.Crystal 2 is also orthorhombic with the same space group, a=11.197(2), b=13.102(2), c=22.402(2) Angstroem, and Z=4.In 1, the d-tart ion makes a familiar face-to-face contact with the Lambda complex, in which the two alcoholic and one carboxylic O atoms of the d-tart ion are involved in the multiple hydrogen bonds to the three H-N groups on the triangular face of the complex.This contact mode resembles the one found earlier in the chloride d-tart salt of the corresponding Lambda Co(III) complex, Lambda-lel3-Cl(d-tart)*2H2O (3).On the other hand, no such face-to-face contact is present in 2, though it has been found in the corresponding Lambda Co(III) complex, Lambda-lel3-Cl(d-tart)*2H2O (4) in which the d-tart ion is obliged to rotate the distal carboxylato group so as to avoid the steric repulsion otherwise imposed on it by one of the bulky chxn ligands.Detailed comparison of the above four crystal structures revealed that the packing modes of the respective complex cations and couterions are surprisingly similar to one another, indicating that the absence of such a face-to-face contact in 2 is attributed to the weaker affinity of the d-tart ion for the divalent Lambda Ni(II) complex, rather than to the steric demands of the crystal packing in 2.In 2 are found two deformed contact modes similar to each other, in which the d-tart ion directs its three O atoms to the triangular face, but only one of them is hydrogen-bonded to one or two of the three H-N groups on the triangular face.The d-tart ion thereby avoids the steric repulsion that would be imposed on it if it should make a usual face-to-face contact with the Lambda complex.

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Highly sensitive chiral shift reagent bearing two zinc porphyrins

(Chemical Equation Presented) A new type of chiral receptor (R,R)- or (S,S)-1b with C2 symmetry was synthesized. An induced-fit type of binding behavior of 1b for diamines was revealed by CD spectroscopy. NMR studies demonstrated that 1b can function as a highly sensitive chiral shift reagent for the determination of the enantiomeric purity of chiral diamines, aziridine, and isoxazoline at the microgram level.

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