20840-07-7

Upstream product

• 127404-73-3 (3E)-4-(4-methoxyphenyl)but-3-enoic acid 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 627-27-0 homoalylic alcohol 
• 623-12-1 4-chloromethoxybenzene 
• 51860-45-8 3-hydroxypropyltriphenylphosphonium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 637-69-4 4-Methoxystyrene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 6552-45-0 α-cyclopropyl(4-methoxyphenyl)methanol 
• 54674-84-9 γ-hydroxypropyltriphenylphosphonium chloride 
• 52999-15-2 4-(p-methoxyphenyl)-3-butyn-1-ol 
• 129887-43-0 2-(p-methoxyphenyl)-3-chlorotetrahydrofuran 
• 7152-03-6 p-methoxyphenyl cyclopropyl ketone 

Downstream Products

• 83665-34-3 (E)-4-(p-methoxyphenyl)-3-butenyl 9-phenanthrenecarboxylate 
• 321904-65-8 (3E)-4-(4-methoxyphenyl)but-3-enyl 6-ethoxy-5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylate 
• 689258-74-0 (E)-tert-butyl((4-(4-methoxyphenyl)but-3-en-1-yl)oxy)dimethylsilane 
• 321904-69-2 (3E)-4-(4-methoxyphenyl)but-3-enyl 6-ethoxy-5,6-dihydro-2-methyl-4-oxo-1,4-oxathiin-3-carboxylate 
• 1224951-99-8 (E)-4-(4-methoxyphenyl)but-3-enyl methanesulfonate 
• 1236889-47-6 (E)-1-methoxy-4-(3-phenylbut-1-en-1-yl)benzene 
• 150660-28-9 (E)-1-methoxy-4-(4-phenylbut-1-en-1-yl)benzene 
• 1426692-53-6 3-chloro-2-(4-methoxyphenyl)tetrahydrofuran 

Relevant academic research and scientific papers

Synthesis of tricyclic precursors of cyclitols

Stereoselective syntheses of three tricyclic cyclohexenones are described. These compounds were conceived as novel precursors of synthetic conduritols, quercitols, and inositols because they allow diastereoselective C=O reductions, C=C osmylations, and C=C epoxidations to be performed. These functionalizations created up to three uniformly configured oxygen-bearing stereocenters. One of the follow-up products was a tricycle that was amenable to successive cleavages of its 1,4-dioxane and 1,3-dioxane rings. This rendered the pentaesters of neo-quercitol, which contain five stereogenic C-O bonds, with ds = 85:15. Georg Thieme Verlag Stuttgart New York.

Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va

HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization

A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.

Hypervalent iodine initiated intramolecular alkene dimerisation: A stereodivergent entry to cyclobutanes

The emergence of new methods for the stereoselective synthesis of strained carbocycles is a challenging but worthwhile endeavour. Cyclobutanes, in particular, have attracted the attention of both medicinal chemists and material scientists for their unique properties. Herein, we present a new method that allows access to highly functionalized cyclobutanes with complementary all-trans and trans-cis-trans relative stereochemistry, that could not be accessed before. This approach consists of an intramolecular dimerisation of non-conjugated dienes using an oxidative single electron transfer (SET) process, and is initiated by catalytic amounts of hypervalent iodine reagents. The potential uses of these cyclobutanes is demonstrated with selective functionalization, including the formation of diols and carboxylic acids.

Copper(I)-Catalyzed Enantioselective Intramolecular Aminotrifluoromethylation of O-Homoallyl Benzimidates

In the present paper, the Cu(I)-catalyzed intramolecular aminotrifluoromethylation of O-homoallyl benzimidates with Togni reagent I was reported. O-Homoallyl benzimidates equipped with terminal alkenes produced chiral 1,3-oxazines with high enantioselectivity in the presence of a chiral BOX ligand, and racemic tetrahydro-1,3-oxazepines were obtained in high yields from internal alkene derivatives with a monoprotected amino acid additive under similar conditions.

Syntheses of Polycyclic Tetrahydrofurans by Cascade Reactions Consisting of Five-Membered Ring Selective Prins Cyclization and Friedel-Crafts Cyclization

A novel cascade reaction consisting of a five-membered ring selective Prins cyclization and a subsequent Friedel-Crafts cyclization is reported. Treatment of homocinnamyl alcohols and aromatic aldehydes with BF3·OEt2 in CH2/sub

Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans

The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.

Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols

In refluxing 9 : 1 (v/v) H2O-1,4-dioxane and without an additional catalyst, the rearrangements of various types of cyclopropyl carbinols were attempted. It was found that the reactions generally gave homoallylic alcohols in good to very high chemical yields. Rearrangements of bicyclic or tricyclic cyclopropyl carbinols readily gave the desired ring-expanded cyclic homoallylic alcohols which are difficult to synthesize by other means.

Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans

An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chloro

Hydrogen-bonding-promoted oxidative addition and regioselective arylation of olefins with aryl chlorides

The first, general, and highly efficient catalytic system that allows a wide range of activated and unactivated aryl chlorides to couple regioselectively with olefins has been developed. The Heck arylation reaction is likely to be controlled by the oxidative addition of ArCl to Pd(0). Hence, an electron-rich diphosphine, 4-MeO-dppp, was introduced to facilitate the catalysis. Solvent choice is critical, however; only sluggish arylation is observed in DMF or DMSO, whereas the reaction proceeds well in ethylene glycol at 0.1-1 mol % catalyst loadings, displaying excellent regioselectivity. Mechanistic evidence supports that the arylation is turnover-limited by the oxidative addition step and, most importantly, that the oxidative addition is accelerated by ethylene glycol, most likely via hydrogen bonding to the chloride at the transition state as shown by DFT calculations. Ethylene glycol thus plays a double role in the arylation, facilitating oxidative addition and promoting the subsequent dissociation of chloride from Pd(II) to give a cationic Pd(II)-olefin species, which is key to the regioselectivity observed.