71434-56-5

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 34164-50-6 4-penten-1-ylmagnesium bromide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 1119-51-3 bromopentene 

Downstream Products

• 42543-56-6 1-(4-methoxyphenyl)-1,5-hexanedione 
• 71434-63-4 1-(1-Chloro-hex-5-enyl)-4-methoxy-benzene 
• 1187016-02-9 C₁₈H₂₂O₂ 

Relevant academic research and scientific papers

Anti-Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox-Active Hydrogen Donor

A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3- or N3-containing hyp

Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols

An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza-)alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent-iodine compounds have been compared. I

Site- And enantiodifferentiating C(sp3)-H oxidation enables asymmetric access to structurally and stereochemically diverse saturated cyclic ethers

A manganese-catalyzed site- and enantiodifferentiating oxidation of C(sp3)-H bonds in saturated cyclic ethers has been described. The mild and practical method is applicable to a range of tetrahydrofurans, tetrahydropyrans, and medium-sized cyclic ethers with multiple stereocenters and diverse substituent patterns in high efficiency with extremely efficient site- and enantiodiscrimination. Late-stage application in complex biological active molecules was further demonstrated. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity. The ability to employ ether substrates as the limiting reagent, together with a broad substrate scope, and a high level of chiral recognition, represent a valuable demonstration of the utility of asymmetric C(sp3)-H oxidation in complex molecule synthesis.

Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents

Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.

Asymmetric Cycloetherification by Bifunctional Organocatalyst

Attempts to obtain enantiomerically enriched tetrahydrofuran derivatives via an intramolecular oxy -Michael addition reaction of ?-hydroxyenone is discussed. Despite previous difficulties associated with the asymmetric induction of this reaction, which can proceed even without a catalyst, a highly efficient asymmetric induction was realized using a bifunctional organocatalyst derived from a cinchona alkaloid. The reaction could be extended to ζ-hydroxyenone to yield an optically active tetrahydropyran derivative with a high ee. In these reactions, it is important for the gentle acidic and basic sites in the bifunctional organocatalyst to be arranged properly within the molecular skeleton of the catalyst. The high performance asymmetric induction relied on the affinity of the catalyst for the substrate, which played an important role. A disubstituted tetrahydropyran synthesis could be effectively performed via kinetic resolution using ζ-hydroxyenone containing a secondary alcohol moiety using a chiral phosphoric acid catalyst.

Asymmetric cycloetherification via the kinetic resolution of alcohols using chiral phosphoric acid catalysts

In this study, novel asymmetric cycloetherification via the kinetic resolution of secondary or tertiary alcohols using chiral phosphoric acid catalysts was developed, affording tetrahydropyrans (THPs) with two stereogenic centers. The cyclization of the recovered optically active alcohols afforded other stereoisomers of THPs. These protocols offer efficient synthetic routes to various optically active THP derivatives, which are important structures found in a range of biologically active agents.

Studies on the amino-heck reactions of unsaturated ketones o-phosphinyloximes for the preparation of substituted pyridines

The amino-Heck cyclization process has been applied into a range of γ,δ-unsaturated ketone O-diethylphosphinyloximes 1 and δ,ε-unsaturated ketone O-diethylphosphinyloximes 7. Under the specific catalytic conditions developed by us, these substrates were found to preferentially undergo the 6-endo cyclization to give the formation of 2-substituted pyridines 3 and substituted methylpyridines 8, respectively, in moderate to good yields. Besides, several interesting aspects on the effects of phosphinyl groups, solvents, bases and molecular sieves on the regioselectivity of the cyclization of 1 have also been realized.

Carbocationic n-endo-trig cyclizations

Unsaturated benzyl cations (4-MeOC6H4)CH +-(CH2)n-CH=CH2 (1) have been generated laser-flash photolytically in acetonitrile in the presence of enol ethers or 2-methylfuran. The reactions of the cations 1 (n = 2 and 4) with these π-nucleophiles follow second-order rate laws with rate constants comparable to those of the analogous saturated species (4MeOC6H 4)CH+-(CH2)3CH3. Product studies show the absence of cyclization products. In contrast, the carbocation (4-MeOC6H4)CH+-(CH2) 3-CH=CH2 (Id) undergoes a highly reversible 6endo-trig cyclization which is approximately 107 times faster than the corresponding intermolecular reaction of (4MeOC6H4)CH +-(CH2)3CH3 with hex1-ene. This cyclization yields a highly electrophilic, partially bridged carbocation, which accounts for the finding that Id is consumed eight times faster in trifluoroethanol solution than all other carbocations of this series. Quantum-chemical calculations (B3LYP/6311G(d,p) and MP2/6-31+G(2d,p)) have been performed to elucidate the structures of the involved carbocations. Consequences of these findings on the role of π-participation in solvolysis reactions are discussed.

Pyridine compounds for treating leukotriene-related diseases

STR1 This invention relates to compounds of formula (I) which are useful as leukotriene antagonists.

Titanium- or Zirconium-Catalyzed Selective Dehydrogenation of Benzyl Alcohols to Aldehydes and Ketones with tert-Butyl Hydroperoxide

Primary and secondary benzyl alcohols are selectively converted in high yields into the corresponding aldehydes or ketones using tert-butyl hydroperoxides and catalytic amounts of titanium or (better) zirconium alcoholates.Aliphatic hydroxy groups, double bonds (except those in allylic position to hydroxy groups), and phenolic hydroxy groups (except those in the ortho position to the benzylic alcohol) are not attacked.