58547-18-5

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 6407-36-9 N-isopropyliden-cyclohexyl amine 
• 67-64-1 acetone 
• 1118-84-9 allyl acetoacetate 
• 78-95-5 chloroacetone 
• 108-22-5 Isopropenyl acetate 
• 58547-15-2 2,2,2-trichloroethyl 3-oxobutanoate 

Downstream Products

• 33046-41-2 (E)-6-phenyl-3-hexen-2-one 
• 93643-64-2 (S)-4-hydroxy-6-phenylhexan-2-one 
• 62627-08-1 4-acetoxy-6-phenylhexan-2-one 
• 127841-38-7 5-hydroxy-1,1-dimethoxy-7-phenyl-3-heptanone 
• 89762-92-5 syn-5-benzyloxyimino-1-phenyl-3-hexanol 
• 69172-23-2 5H-r,trans-3-hydroxy-cis-3-methyl-7-phenylheptan-5-olide 
• 69172-23-2 5H-r,cis-3-hydroxy-trans-3-methyl-7-phenylheptan-5-olide 
• 89763-02-0 syn-5-amino-1-phenyl-3-hexanol 
• 89763-02-0 anti-5-amino-1-phenyl-3-hexanol 
• 75677-81-5 ethyl 5-acetoxy-3-hydroxy-3-methyl-7-phenylheptanoate 
• 107977-21-9 cis-4-methyl-6-phenethyltetrahydro-2H-1,3-oxazin-2-one 

Relevant academic research and scientific papers

Improved conditions for the proline-catalyzed aldol reaction of acetone with aliphatic aldehydes

The proline-catalyzed asymmetric aldol reaction between aliphatic aldehydes and acetone has, to date, remained underdeveloped. Challenges in controlling this reaction include avoiding undesired side reactions such as aldol condensation and self-aldolization. In recent years we have developed optimized conditions, which enable high yields and good to excellent enantioselectivities, and which are presented in this communication. Georg Thieme Verlag Stuttgart New York.

Ti-catalyzed reformatsky-type coupling between α-halo ketones and aldehydes

(Chemical Equation Presented) We describe the first Ti-catalyzed Reformatsky-type coupling between α-halo ketones and aldehydes. The reaction affords β-hydroxy ketones under mild, neutral conditions compatible with ketones and other electrophiles. The cat

Decarboxylative aldol reactions of allyl β-keto Esters via heterobimetallic catalysis

Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl β-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl β-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis in which the optimized reaction conditions require the addition of both metals. Copyright

A highly chemoselective Mukaiyama aldol reaction of saturated aldehyde over unsaturated aldehyde with enol tris(2,6-diphenylbenzyl)silyl ether

An exceedingly high chemoselective Mukaiyama aldol reaction of saturated aldehydes in the presence of unsaturated aldehydes (benzaldehyde and α,β-enals) has been realized for the first time by using the structurally unique enol tris(2,6-diphenylbenzyl)sil

Chemically reactive immunogens lead to functional convergence of the immune response

An aldolase antibody, 24H6, which was obtained from immunization with the large hapten 2, is shown to possess an active-site lysine residue with a perturbed pK(a) of 7.0. This antibody catalyzes both the aldol addition and the retrograde aldol fragmentation with a broad range of substrates that are structurally different from the hapten. This observation suggests that in reactive immunization with 1,3-diketones, the hapten structure governs the chemistry but not the overall organization of the active site. Hammett correlation studies of the 38C2- and 24H6-catalyzed aldol and retroaldol reactions revealed that although the two antibodies exhibit broad substrate specificities, they utilize slightly different mechanisms. While antibody 38C2 adopts a mechanism that is reminiscent of an acid-catalyzed aldol reaction, antibody 24H6 follows a mechanism that is similar to the base-catalyzed reaction.

Diethylaluminum ethoxide mediated crossed aldol reaction of enol esters with carbonyl compounds

Crossed aldol reaction of enol esters, stable carbon nucleophiles, with carbonyl compounds is effectively performed by the promotion of diethylaluminum ethoxide under mild conditions. This reaction is applicable not only to simple enol esters but also to

Chemistry of aldolate dianions. Effects of β-heteroatom substituents on ketone enolization

β-Hydroxy ketones can be doubly deprotonated with >2 equiv of an amide base at low temperature providing both proximal or distal aldolate dianions in good to excellent yield. A variety of substitutionally biased β-hydroxy ketones give exclusively distal dianions. If the distal site is blocked, proximal dianions are formed in good yield; however, Chromatographic separation of the silylated products leads to decreased yields. Comparative enolization studies of 4-hydroxy-2-butanone, l-hydroxy-3-pentanone, and hydroxyl-substituted derivatives reveal a kinetic factor favoring proximal deprotonation of β-OTMS and β-alkoxy ketones. However, there is a thermodynamic factor favoring distal dianions that becomes significant as solutions of the dianions are warmed. Thermal stability studies indicate good room temperature stability of the dianions toward elimination and retroaldolization processes; control studies in this area also support the presence of a dianionic species. Precedent suggests that the dianions exist as internally chelated species, and we speculate that ion triplets containing bridging lithiums are good candidates for the structure of both proximal and distal dianion species. The distal dianions undergo clean reaction with aldehydes and acyl cyanides leading to β,β′-dihydroxy ketones and β-hydroxy-β′-oxo ketones, respectively.

Asymmetric aldol reactions using (4R-trans)-2-(1-methylethenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid, bis-ethyl ester, a chiral precursor of the acetone enolate

(4R-trans)-2-(1-Methylethenyl)-1,3,2-dioxaborolane-4,5-dicarboxylic acid, bis-ethyl ester upon oxidation with trimethylamine oxide gives a chiral enol borate that condenses with aldehydes to give optically active 4-hydroxy-2-alkanones in 55-77percent yield and 41-65percent e.e.

Stereoselective Preparation of Acyclic syn-β-Amino Alcohols from β-Hydroxy Ketones via the Corresponding O-Benzyl Oximes

Reduction of β-hydroxy ketone O-benzyl oximes with lithium aluminum hydride in the presence of sodium or potassium methoxide afforded the corresponding syn-β-amino alcohols in highly stereoselective manner.A lythraceae alkaloid, lasubine II, was synthesiz