35544-95-7

Upstream product

• 25112-78-1 2-methyl-2-(3-oxobutyl)-1,3-cyclopentanedione 
• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 78-94-4 methyl vinyl ketone 
• 344-25-2 D-Prolin 

Downstream Products

• 17553-86-5 (R)-7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione 
• 17553-86-5 (S)-Halos-Parish ketone 

Relevant academic research and scientific papers

AN APPROACH TO STEREOSELECTIVE FORMATION OF GLYCINOECLEPIN A SIDE CHAIN

Claisen rearrangement was found to be an efficient method for the stereoselective construction of the glycinoeclepin A side chain.

An unconventional approach to the enantioselective synthesis of caryophylloids

The chiral enones 4 and ent-4 have been synthesized enantiomerically as configurationally stable compounds that can be used for the synthesis of caryophylloids. For instance, ent-4 has been converted to the marine natural product coraxeniolide A. Copyright

Evaluating β-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction

A systematic study of the effect of substitution within the β-amino acid framework indicates that both β2- and β3- amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained β-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to l-proline. The Royal Society of Chemistry.

Catalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by cis- and trans-4,5-methanoprolines: Sensitivity of proline catalysis to pyrrolidine ring conformation

Methanoprolines are found to be catalysts for the Hajos-Parrish-Eder-Sauer- Wiechert reaction.[1] cis-4,5-Methanoproline exhibits catalytic ability similar to proline (86% yield, 93% ee), whereas the trans-4,5- methanoproline is less selective (67% yield, 83% ee) and shows less acceleration. The reaction was also studied with hybrid density functional theory (B3LYP). The nearly planar cis-4,5-methanoproline amine better reflects the planar iminium of the transition states than the pyramidalized trans4,5-methanoproline. This difference in conformation is responsible for the observed higher enantioselectivity and enhanced catalytic behavior of the cis-4,5-methanoproline.

Inotropic activity of hydroindene amidinohydrazones

Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na+,K+ ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human α2β1 isozyme (associated with the inotropic effect) with respect to the α1β1 isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).

Asymmetric one-pot Robinson annulations

One-pot syntheses of ketol SS-5a, enone S-2 and optically active spiroenediones S-14, R-7 and S-15 are reported.

Use of Winterfeldt's template to control the C-2' configuration in the synthesis of strigol-type compounds

A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues.

Asymmetric Michael addition of malonate anions to prochiral acceptors catalyzed by L-proline rubidium salt

L-Proline rubidium salt catalyzes the asymmetric Michael addition of malonate anions to prochiral enones and enals. This method can be applied to a wide range of substrates to give adducts with a predictable absolute configuration: (S)-adducts from (E)-enones/enals and (R)-adducts from cyclic (Z)-enones. Both the secondary amine moiety and the carboxylate moiety are critical for the catalytic activity and asymmetric induction. Varying the countercation also affects the reaction course. High enantiomeric excesses were attained when di(tert-butyl) malonate was added to (E)-enones in the presence of CsF. The stereochemistry of the Michael reaction indicates that asymmetric induction takes place via enantioface discrimination involving the acceptor α-carbon atom rather than the β-carbon atom.

Nonlinear Effects in Asymmetric Synthesis. Examples in Asymmetric Oxidations and Aldolization Reactions

It has been shown in three experiments that there is a strong departure from the linear relationship usually assumed between the enantiomeric excess of a chiral auxiliary and the extent of the asymmetric synthesis.This gives useful information on the reac

Asymmetric synthesis of organic compounds

Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a "meso" type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.