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• 24892-80-6 2-(1-phenylvinyl)anisole 
• 883-90-9 o-benzyl anisole 
• 80-48-8 methyl p-toluene sulfonate 
• 74-88-4 methyl iodide 
• 40473-50-5 2-(hydroxy(phenyl)methyl)phenol 
• 100-42-5 styrene 
• 5720-06-9 2-Methoxyphenylboronic acid 

Relevant academic research and scientific papers

Asymmetric synthesis of diarylmethane derivatives by dynamic kinetic resolution

Abstract Asymmetric allylation of ortho-methoxydiphenylmethane has been carried out with high yields and ee of up to 94% using the chiral ligand (-)-sparteine as an additive. Results of reactions performed under various conditions suggest that a dynamic k

Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes

The enantioselective hydroarylation of vinylarenes catalyzed by a chiral, non-racemic nickel catalyst is presented as a facile method to generate chiral 1,1-diarylethanes. These reactions proceed via formation of a chiral, non-racemic nickel benzyl intermediate. Transmetalation with arylboron nucleophiles and subsequent reductive elimination enable the formation of a variety of chiral 1,1-diarylethanes. The 1,1-diarylethane products from reactions of arylboronic acids containing electron-donating substituents are formed with typically greater than 90% ee, while the 1,1-diarylethanes generated from reactions of arylboronic acids containing electron-withdrawing groups are generated with typically less than 80% ee. These results are consistent with the rate of transmetalation with an arylboron nucleophile playing a key role in the enantioselectivity of these hydroarylation reactions. This mechanistic insight has led to the development of reactions of neo-pentylglycolate esters of arylboronic acids with vinylarenes that occur with higher enantioselectivities based on increased rates of transmetalation.

Chiral Iridium Complexes of Anionic NCP Pincer Ligand for Asymmetric Transfer Hydrogenation of 1,1-Diarylethenes with Ethanol

Chiral iridium complexes ligated by anionic oxazoline-bearing NCP-type pincer ligands were developed and applied to the asymmetric transfer hydrogenation (ATH) of diarylethenes using environmentally benign ethanol as the hydrogen donor. High enantioselectivities could be achieved for substrates bearing ortho-Me, ortho-Cl, or ortho-Br substituents on one of the aryl groups. The ATH of ortho-Br-substituted diarylethenes is particularly attractive due to the propensity of the C(aryl)-Br bond to undergo various new bond-forming events.

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Organocatalytic Asymmetric Nucleophilic Addition to o-Quinone Methides by Alcohols

The first catalytic asymmetric intermolecular alcohol conjugate addition to o-quinone methides (o-QMs) is disclosed. Due to reversible C-O bond formation and low nucleophilicity of alcohols, catalytic asymmetric oxa-Michael additions with simple alcohol nucleophiles to establish acyclic oxygenated carbon stereocenters remain scarce. The present reaction represents a rare example of this type. With a suitable chiral acid catalyst, the in situ formation of o-QMs and subsequent conjugate addition proceeded with high efficiency and enantioselectivity. The chiral ether products are versatile precursors to other chiral molecules.

Highly enantioselective hydrogenation of styrenes directed by 2′-hydroxyl groups

A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by installing a 2′-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2′-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

Enantioselective preparation of 1,1-diarylethanes: Aldehydes as removable steering groups for asymmetric synthesis

Cut it out! Convenient procedures have been delineated for the synthesis of optically active, functionalized 1,1-diaryl-ethanes by decarbonylation of β,β-diaryl-propionaldehydes. The process can be conducted as a one-pot 1,4-addition/decarbonylation sequence. Aldehydes are used as removable steering groups in this new strategy for the preparation of optically active building blocks. (Chemical Equation Presented)