173975-68-3

Upstream product

• 930-68-7 cyclohexenone 
• 2043-61-0 cyclohexanecarbaldehyde 
• 17814-55-0 trichloro<(1-cyclohexenyl)oxy>silane 
• 22780-11-6 1-(2,2,2-trichloroacetoxy)cyclohexene 
• 108-94-1 cyclohexanone 

Downstream Products

• 24195-40-2 2-(cyclohexylmethylidene)cyclohexanone 

Relevant academic research and scientific papers

Highly enantioselective co-catalytic direct aldol reactions by combination of hydrogen-bond donating and acyclic amino acid catalysts

Highly enantioselective co-catalytic direct aldol reactions by a combination of simple hydrophobic acyclic amino acid and hydrogen-bond donating catalysts are presented. The corresponding aldol products are formed in high yields with high regio-, diastere

Reversal of enantioselectivity in aldol reaction: New data on proline/λ-alumina organic-inorganic hybrid catalysts

We report new results on the aldol reactions between aldehydes of three different types (aromatic, aliphatic and cycloaliphatic) and acetone/cycloalkanones as reaction partners, driven by organic-inorganic hybrid catalyst Pro/λ-Al2O3. In contrast to the homogeneous liquidphase reaction, over Pro/λ-Al2O 3reversal of the enantioselection in up to 20-40 % ee depending on the structure of the aldehyde was observed in reactions of acetone. Reversal of the ee in the presence of c-Al2O3cannot be generalized, as it has only been observed for acetone among the ketones studied by us. It was proven using methods of a great variety such as ultrasonic irradiation, reuse measurements on used catalyst and the filtrate of the first reaction, measurements on the L-Pro-L-Pro(OH) dipeptide, studies using mixtures of L-Pro and D-Pro that the organic-inorganic hybrid catalyst Pro/λ-Al 2O3formed in situ is responsible for reversal of the ee. In the reactions of cycloalkanones there is presumably competition between the liquid-phase and the surface reaction over Pro/ c-Al2O 3with preference for the former. Based on these results a surface reaction pathway was proposed. Although, the ees obtained under heterogeneous catalytic conditions are low, further studies may lead to application of this unusual phenomenon for obtaining chiral heterogeneous catalysts suitable for the preparation of the desired enantiomer of a chiral compound using the same chiral source. Springer Science+Business Media New York 2013.

L-proline/CoCl2-catalyzed highly diastereo- and enantioselective direct aldol reactions

The CoCl2/L-proline (1:2) system was found to be an excellent catalyst for direct aldol reactions. Excellent yields (up to 93 %) and a significant improvement in diastereoselectivity (anti/syn up to 45:1) as well as enantioselectivity (up to mo

Highly efficient small organic molecules for enantioselective direct aldol reaction in organic and aqueous media

(Chemical Equation Presented) A series of highly efficient organocatalysts have been derived from naturally available amino acids for carrying out enantioselective direct aldol reaction in both organic and aqueous medium. The aldol products were obtained in high diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee) for a broader range of substrates using 1 mol % of a catalyst. The results demonstrate that the structural features of organocatalysts play a crucial role in obtaining high optical purity of aldol adducts in an aqueous medium. Further, the role of water in increasing the rate and enantioselectivity of the reaction has been illustrated. Moreover, the aldol products have been employed in the synthesis of chiral amino alcohols which act as useful intermediates for building up complex natural products.

Highly diastereo- and enantioselective direct aldol reactions in water

(Chemical Equation Presented) Going green: The synthetically very important aldol reaction can proceed in water without a metal catalyst with excellent enantioselectivity. The key to the reaction is a small, synthetic organic catalyst based on trans-hydroxyproline with a siloxy group. Thus, this method is an environmentally friendly process for the synthesis of chiral molecules.

Dibutyltin dimethoxide-catalyzed aldol reaction of enol trichloroacetates

A catalytic aldol condensation of aldehydes with enol trichloroacetates was achieved using dibutyltin dimethoxide as a novel catalyst in a mixed solvent consisting of THF and MeOH. Various β-hydroxy ketones were diastereoselectively obtained in high yields up to 99%.

Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects

Trichlorosilyl enolates of ketones (enoxytrichlorosilanes) were demonstrated to be highly reactive aldol addition reagents. Trichlorosilyl enolates of cyclohexanone (E-enolate) and propiophenone (Z-enolate) reacted readily at room temperature with a wide

INTERMOLECULAR ALDOL REACTIONS VIA ALLYLIC O-STANNYL KETYLS

A mild and neutral free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate.A tin(IV)enolate, produced by subsequent hydrogen atom transver, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new α,β-unsaturated ketones with E/Z ratios up to > 100:1.