51384-73-7

Upstream product

• 68204-17-1 3-phenylbut-2-enoyl chloride 
• 18815-73-1 methylzinc iodide 
• 141-78-6 ethyl acetate 
• 71-43-2 benzene 
• 20192-94-3 (3E)-4-ethoxypent-3-en-2-one 
• 917-54-4 methyllithium 
• 20698-78-6 (+/-)-3-Methoxy-3-phenyl-buttersaeure 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 98-86-2 acetophenone 
• 78840-03-6 2-phenyl-4-ethylthio-2-pentene 
• 49784-51-2 4-chloropent-3-en-2-one 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 5158-46-3 methylzinc chloride 
• 591-50-4 iodobenzene 

Downstream Products

• 1207736-65-9 1,3-dimethyl-1-phenyl-1H-benzo[f]chromene 
• 1592890-25-9 (E)-(4-methylhepta-1,5-dien-4-yl)benzene 
• 1592890-27-1 (E)-(4-methylhepta-2,6-dien-2-yl)benzene 
• 104174-53-0 4-phenyl-3-penten-2-ol 
• 15121-66-1 4-Hydroxy-4-phenyl-2-pentanone 
• 827-69-0 (E)-4-phenyl-3-penten-2-one 
• 856-15-5 4-phenyl-pent-3-en-2-one-(2,4-dinitro-phenylhydrazone) 
• 32587-80-7 (S)-4-phenylpentan-2-one 
• 67110-72-9 (4R)-4-phenylpentan-2-one 
• 17913-10-9 1-methyl-3-phenyl-butanal 
• 4467-33-8 6-methyl-4-phenyl-2H-pyran-2-one 
• 106538-99-2 (R)-4-hydroxy-4-phenylpentan-2-one 
• 36567-70-1 (3R)-3-phenyl-3-hydroxybutanoic acid 
• 1239568-87-6 (S)-4-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one 

Relevant academic research and scientific papers

Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols

The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.

Lewis Acid Catalyzed Ring-Opening Reaction of Cyclobutanones towards Conjugated Enones

An unprecedented Fe-catalyzed ring-opening reaction of simple cyclobutanones is developed, which provides access to conjugated enones with good functional group tolerance in high yields under mild conditions. The product derivatization and gram-scale expe

Rearrangement Reactions Leading to Optically Active α,α-Disubstituted Primary Allylamines

Synthetic routes to α,α-disubstituted allylamines have been examined. Racemic compounds were conveniently prepared by thermal Overman rearrangements of primary allylic alcohols with trisubstituted double bonds, but rearrangement of these substrates using

Tuning the Reactivity of Functionalized Diallylic Alcohols: Br?nsted versus Lewis Acid Catalysis

The chemodivergent reactivity of bifunctional, enol thioether-containing diallylic alcohols in acidic medium is disclosed, highlighting the difference between strong Lewis acid and mild Br?nsted acid catalysis. In the presence of bismuth(III) triflate, allylic alcohol activation affords diversely substituted cyclopentenones in a Nazarov-type electrocyclization, whereas activation of the thioenol ether by p-toluenesulfonic acid provides an entry to α-sulfenylated β,γ-unsaturated ketones. Both methods represent a facile access to the corresponding products under mild conditions, using inexpensive and non-toxic catalytic systems.

Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with allylB(pin)

Application of internal electrophiles in catalytic stereospecific allyl-allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation ca

Enantioselective synthesis of quaternary carbon stereogenic centers through copper-catalyzed conjugate additions of aryl- and alkylaluminum reagents to acyclic trisubstituted enones

Acyclic quaternary carbons by conjugate addition: The first examples of catalytic enantioselective conjugate additions of aryl and alkyl units that generate acyclic all-carbon quaternary stereogenic centers have been developed (see scheme). The requisite

Features of the chromatography-mass spectrometric identification of condensation products of the carbonyl compounds

By the example of the condensation products of acetone with the simplest aromatic carbonyl compounds it was shown that the joint interpretation of mass spectrometric and chromatographic data in conjunction with a priori assumptions about the nature of the chemical structure allows the detection of the components of reaction mixtures that were not previously characterized by standard mass spectra or by retention indices on standard stationary phases. A necessary condition for solving such problems is creating a hypothesis about the sample composition that is possible for the expected products of the known organic reactions.

Preparation and decarboxylative rearrangement of (Z)-enyne esters

A method to assemble (Z)-enyne esters via palladium-catalyzed cross coupling reactions of enol tosylates is reported. A base-mediated one-pot decarboxylative rearrangement of the enynes to enones is described. The scope of this process is examined.

Asymmetric conjugate reduction of α,β-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

New asymmetric conjugate reduction of β,β-disubstituted α,β-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high enantioselectivity. (E)-4-Phenyl-3-penten-2- one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60°C in 95% ee and 98 % ee, respectively, by 1 mol % of catalyst loading. (EtO) 2MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-β-methylcinnamate and β-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98% ee.

Enantioselective epoxidation with chiral MnIII(salen) catalysts: Kinetic resolution of aryl-substituted allylic alcohols

A set of aryl-substituted allylic alcohols rac-2 has been epoxidized by chiral Mn(salen*) complexes 1 as the catalyst and iodosyl benzene (PhIO) as the oxygen source. Whereas one enantiomer of the allylic alcohol 2 is preferentially epoxidized to give the threoor cis-epoxy alcohol 3 (up to 80% ee) as the main product (dr up to >95:5), the other enantiomer of 2 is enriched (up to 53% ee). In the case of 1,1-dimethyl-1,2-dihydronaphthalen-2-ol (2c), the CH oxidation to the enone 4c proceeds enantioselectively and competes with the epoxidation. The absolute configurations of the allylic alcohols 2 and their epoxides 3 have been determined by chemical correlation or CD spectroscopy. The observed diastereo- and enantioselectivities in the epoxidation reactions are rationalized in terms of a beneficial interplay between the hydroxy-directing effect and the attack along the Katsuki trajectory.