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Relevant academic research and scientific papers

Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach

A cyanide-free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed for the enantiospecificity that is usually not observed in enzyme catalysis. Depending on whether the E or Z isomer of the racemic aldoxime substrate was employed, one or the other enantiomer of the corresponding nitrile was formed preferentially with the same enzyme.

Iridium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted Nitroalkenes

A highly efficient, iridium-catalyzed, enantioselective hydrogenation of β,β-disubstituted nitroalkenes has been developed. Using a complex consisting of iridium and (S,S)-f-spiroPhos as the catalyst, a variety of β,β-disubstituted nitroalkenes were successfully hydrogenated to the corresponding chiral nitroalkanes with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON=1000).

Rh-catalyzed highly enantioselective hydrogenation of nitroalkenes under basic conditions

Go catalytic! A highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes and isomeric mixtures of nitroalkenes by using a Rh/DuanPhos catalytic system under basic conditions has furnished a convenient approach to β-chiral nitroalkanes, whic

Efficient synthesis of hydroxyl isoindolones by a Pd-mediated C-H activation/annulation reaction

Radical reaction: A convenient synthesis of hydroxyl isoindolones by a Pd-catalyzed C-H activation/annulation reaction with near "click chemistry" efficiency is presented (see scheme; TBHP=tert-butyl hydrogen peroxide). This methodology features short reaction times (10-30 min), high atom economy, wide substrate scope (22 examples), and good reaction yields (up to 93 %). Copyright

Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes

Building the building blocks: A highly enantioselective hydrogenation of ?-aryl-?-alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.

Chemoselective and enantioselective transfer hydrogenation of Β, Β-disubstituted nitroalkenes catalyzed by a water-insoluble chiral diaminerhodium complex in water

Asymmetric transfer hydrogenation of Β, Β-disubstituted nitroalkenes catalyzed by a chiral diaminerhodium complex in combination with HCO2NaHCO2H as a hydrogen source in water was successfully realized with high reactivity, excellent chemoselectivity and good enantioselectivity. The metal precursor and pH value of the aqueous solution have a large influence on the reactivity and chemoselectivity. The substituents on the benzene rings and the sulfonyl groups of TsDPEN have significant effects on the enantioselectivity. This catalytic asymmetric transformation is one of the most practical pathways to obtain optically active nitroalkanes.

Transfer hydrogenation in water: Enantioselective, catalytic reduction of (E)-β,β-disubstituted nitroalkenes

A mild catalytic asymmetric transfer hydrogenation of β,β- disubstituted nitroalkenes Is reported. Formic acid Is used as a reductant in combination with an Ir catalyst. The reaction Is conducted in water at low pH and open to air to give adducts In prepa

Highly enantioselective reduction of β,β-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes

(Chemical Equation Presented) This is the first report of the use of Clostridium sporogenes extracts for enantioselective reduction of C=C double bonds of β,β-disubstituted (1) and α,β-disubstituted nitroalkenes (3). Crude enzyme preparations reduced aryl derivatives 1a-e and 1h, in 35-86% yield with ≥97% ee. Reduction of (E)- and (Z)-isomers of 1c gave the same enantiomer of 2c (≥99% ee). In contrast, α,β- disubstituted nitroalkene 3a was a poor substrate, yielding (S)-4a in low yield (10-20%), and the ee (30-70% ee) depended on NADH concentration. An efficient synthesis of a library of nitroalkenes 1 is described.

Structure-based insight into the asymmetric bioreduction of the C=C double bond of α,β-unsaturated nitroalkenes by pentaerythritol tetranitrate reductase

Biocatalytic reduction of α- or β-alkyl-barylnitroalkenes provides a convenient and efficient method to prepare chiral substituted nitroalkanes. Pentaerythritol tetranitrate reductase (PETN reductase) from Enterobacter cloacae st. PB2 catalyses the reduction of nitroolefins such as 1-nitrocyclohexene (1) with steady state and rapid reaction kinetics comparable to other old yellow enzyme homologues. Furthermore, it reduces 2-aryl-1-nitropropenes (4a-d) to their equivalent (S)-nitropropanes 9a-d. The enzyme shows a preference for the (Z)-isomer of substrates 4a-d, providing almost pure enantiomeric products 9a-d (ees up to > 99%) in quantitative yield, whereas the respective (E)-isomers are reduced with lower enantioselectivity (63-89% ee) and lower product yields. 1-Aryl-2-nitropropenes (5a, b) are also reduced efficiently, but the products (R)-10 have lower optical purities. The structure of the enzyme complex with 1-nitrocyclohexene (1) was determined by X-ray crystallography, revealing two substrate-binding modes, with only one compatible with hydride transfer. Models of nitropropenes 4 and 5 in the active site of PETN reductase predicted that the enantioselectivity of the reaction was dependent on the orientation of binding of the (E)- and (Z)- substrates. This work provides a structural basis for understanding the mechanism of asymmetric bioreduction of nitroalkenes by PETN reductase.

Asymmetric Reduction of Nitro Olefins by Fermenting Bakers' Yeast

Reduction of a number of 1-nitro-1-alkenes by fermenting bakers' yeast has been found to be enantioselective, resulting in the formation of optically active 1-nitroalkanes.In most cases, optical purities of the products determined by HPLC analysis of MTPA amides were as high as 83-98percent ee.The optimum rate of conversion was obtained when the reaction was carried out at pH 8 and low concentration of substrates.The absolute configuration of resulting (+)-1-nitro-2-phenylpropane was determined to be R by comparing the specific rotation with that of an authentic specimen after reductive hydrolysis to the corresponding aldehyde.