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• 17874-17-8 cyclohex-1-enyl-trimethyl-silane 
• 17814-55-0 trichloro<(1-cyclohexenyl)oxy>silane 
• 71444-29-6 (2RS)-2-[(RS)-hydroxy-(4-nitrophenyl)methyl]cyclohexanone 
• 67-64-1 acetone 

Relevant academic research and scientific papers

An investigation of chiral diamides as organocatalysts in asymmetric aldol reaction

Seven novel proline and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (THIQA) based diamides were synthesized successfully by simple amidation reactions and characterized by their spectral data. Their catalytic activities in asymmetric aldol reaction w

Recyclable Helical Poly(phenyl isocyanide)-Supported l-Proline Catalyst for Direct Asymmetric Aldol Reaction in Brine

Abstract: A novel helical poly(phenyl isocyanide) bearing Boc protected l-proline pendants (poly-1m) was designed and synthesized. Removed the protecting Boc groups on the l-proline pendants led to the formation of helical polymer poly-2m, which showed high optical activity owing to the preferred right-handed helix of polyisocyanide main chain. Optically active helical poly-2m showed excellent catalytic ability on asymmetric aldol reaction. Helical polymer catalysts exhibited enhanced stereoselectivity in aldol reaction compared to small molecule l-proline. Under the optimized aldol reaction condition, the enantiomeric excess (ee) and diastereomeric ratio (dr) values of the aldol reaction product were respectively up to 90% and > 20/1. Moreover, the helical polyisocyanide catalyst Poly-2m can be easily recovered and reused in the aldol reaction for at least five cycles with maintained its activity and stereoselectivity. Graphic Abstract: Enantioselective aldol reaction catalyzed by poly-2m.[Figure not available: see fulltext.]

Synthesis of Chiral o -Aminobenzylamines by Stereoselective Addition of Grignard Reagents to N -[(o -Aminophenyl)methylene] sulfinamides

Chiral o-aminobenzylamines are synthons for many chiral ligands and catalysts that have been widely used in asymmetric synthesis. Here, we report a highly efficient and stereoselective addition of Grignard reagents to N -[(o -aminophenyl)methylene]sulfinamides to give a range of o -aminosulfinylimines in good yields with good to excellent diastereoselectivities.

New small γ-turn type: N -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes

New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn?:?anti/13?:?87 dr, up to 99% ee). This journal is

L-proline functionalized pillar-layered MOF as a heterogeneous catalyst for aldol addition reaction

A pillar-layered proline-functionalized MOF, [Zn2(2,6-ndc)2(bpb-NHPro)] (I), was synthesized through a solvothermal reaction of Zn(NO3)2 with 1-L-Pyrrolidine-2-carboxamide-2, 5-bis(4-pyridyl)benzene (bpb-NHPro) and 2,6-naphthalenedicarboxylic acid (H2ndc) in N,N-diethyl formamide (DEF). The aldol addition between cyclopentanone and 4-nitrobenzaldehyde was selected as a model reaction for the estimation of the catalytic performance of I, which showed reversed diastereoselectivity, preferring syn-adduct, in contrast to homogeneous catalysis with excellent yield up to 98% and diastereomeric excess up to 98:2 (syn:anti).

Catalytic Gels for a Prebiotically Relevant Asymmetric Aldol Reaction in Water: From Organocatalyst Design to Hydrogel Discovery and Back Again

This paper reports an investigation into organocatalytic hydrogels as prebiotically relevant systems. Gels are interesting prebiotic reaction media, combining heterogeneous and homogeneous characteristics with a structurally organized active solid-like catalyst separated from the surrounding environment, yet in intimate contact with the solution phase and readily accessible via liquid-like diffusion. A simple self-assembling glutamine amide derivative 1 was initially found to catalyze a model aldol reaction between cyclohexanone and 4-nitrobenzaldehyde, but it did not maintain its gel structure during reaction. In this study, it was observed that compound 1 could react directly with the benzaldehyde to form a hydrogel in situ based on Schiff base 2 as a low-molecular-weight gelator (LMWG). This new dynamic gel is a rare example of a two-component self-assembled LMWG hydrogel and was fully characterized. It was demonstrated that glutamine amide 1 could select an optimal aldehyde component and preferentially assemble from mixtures. In the hunt for an organocatalyst, reductive conditions were applied to the Schiff base to yield secondary amine 3, which is also a highly effective hydrogelator at very low loadings with a high degree of nanoscale order. Most importantly, the hydrogel based on 3 catalyzed the prebiotically relevant aldol dimerization of glycolaldehyde to give threose and erythrose. In buffered conditions, this reaction gave excellent conversions, good diastereoselectivity, and some enantioselectivity. Catalysis using the hydrogel of 3 was much better than that using non-assembled 3 - demonstrating a clear benefit of self-assembly. The results suggest that hydrogels offer a potential strategy by which prebiotic reactions can be promoted using simple, prebiotically plausible LMWGs that can selectively self-organize from complex mixtures. Such processes may have been of prebiotic importance.

New Chiral Hydrogen-Bonded Organic Framework Based on Substituted Diarylacetylene Dicarboxylic Acid

A new chiral hydrogen-bonded organic framework (HOF) denoted as ZIOC-1 based on a l-prolineamide substituted diarylacetylene dicarboxylic acid (3,3′-ethyne-1,2-diylbis[6-(l-prolylamino)benzoic acid]) has been synthesized and structurally characterized. Crystal structures of two forms of ZIOC-1, i.e., anhydrous and dihydrate phases, were identified by powder X-ray analysis. It was found that the novel HOF material demonstrated a framework flexibility: its crystalline phases transform reversibly into each other by a change in either humidity or ambient temperature. This fact in conjunction with the retention of crystal identity to the temperature as high as 265 °C indicates a robustness of the framework formed by a hydrogen bonding system. The catalytic performance of the synthesized HOF was probed in aldol condensation and Michael reaction.

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h

Chiral amphiphilic secondary amine-porphyrin hybrids for aqueous organocatalysis

Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, a

New 1D chiral Zr-MOFs based on in situ imine linker formation as catalysts for asymmetric C–C coupling reactions

A novel chiral diimine Zr-MOF (DUT-136, DUT - Dresden University of Technology) is synthesized in a one-pot reaction from ZrCl4, 4-formylbenzoic acid, and (R,R)-1,2-diphenylethylenediamine as an enantiopure core. Inspired by the versatile chemi