85662-51-7

Upstream product

• 75750-06-0 2-phenyl-2-methylcyclobutanone 
• 85662-39-1 1-lithiomethyl phenyl selenoxide 
• 74675-98-2 2-trimethylsilyloxy-5-phenyl-1,5-hexadiene 
• 110458-36-1 (3-Isopropylidene-1-methyl-cyclopentyl)-benzene 
• 157311-37-0 3-Methyl-3-phenyl-hexanedioic acid diethyl ester 
• 3917-20-2 3-phenyl-1-vinyloxybut-2-ene 
• 3810-26-2 3-phenyl-2-cyclopenten-1-one 
• 917-54-4 methyllithium 
• 75-11-6 diiodomethane 
• 151990-53-3 3-methyl-3-phenylcyclobutan-1-one 
• 2758-18-1 3-Methyl-2-cyclopenten-1-one 
• 591-51-5 phenyllithium 
• 101-41-7 benzeneacetic acid methyl ester 
• 98-80-6 phenylboronic acid 

Downstream Products

• 36920-29-3 4-methyl-4-phenylcyclopent-2-en-1-one 
• 65564-94-5 3-Methyl-3-p-nitrophenylcyclopentanon 
• 69849-76-9 3,5-Dimethyl-3-phenylcyclopentanon 
• 33026-43-6 2,2,3-Trimethyl-3-phenylcyclopentanon 
• 131700-53-3 (+)-2-benzylidene-4-methyl-4-phenylcyclopentanone 
• 1401075-93-1 (S)-2-methyl-N-((1R,3R)-3-methyl-3-phenylcyclopentyl)propane-2-sulfinamide 
• 1401075-91-9 (S)-2-methyl-N-((S,3R)-3-methyl-3-phenylcyclopentyl)propane-2-sulfinamide 
• 1401075-96-4 (1S,3R)-3-methyl-3-phenylcyclopentanaminium chloride 
• 131726-64-2 (S)-methyl 3-oxo-1-phenylcyclopentanecarboxylate 

Relevant academic research and scientific papers

Recoverable polystyrene-supported palladium catalyst for construction of all-carbon quaternary stereocenters via asymmetric 1,4-addition of arylboronic acids to cyclic enones

The development of recoverable catalysts based on the combination of synthetically demanding ligands with transition metals attracts a lot of attention, especially from the environmental point of view. In this paper, we describe the preparation of a recoverable polystyrene supported chiral palladium catalyst based on PyOx ligand suitable for asymmetric 1,4-addition of arylboronic acids to cyclic 3-substituted five- and six-membered enones. In the reaction, all?carbon quaternary stereocenters are formed with a high level of enantioselectivity (up to 91% ee) and conversion (up to 99%). The catalyst was used in 6 cycles with no loss of enantioselectivity and only a small decrease in conversion. A solution of the problems associated with the transition from homogeneous to heterogeneous catalytic systems is discussed.

Stepwise approach for sterically hindered Csp3-Csp3 bond formation by dehydrogenative: O -alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes

A stepwise dehydrogenative cross-coupling method was developed for the formation of sterically hindered Csp3-Csp3 bonds. Intramolecular dehydrogenative O-alkylation of a β-ketoester by 2,3-dichloro-5,6-dicyano-p-benzoquinone to form an oxolane followed by Lewis acid-catalyzed [1,3]-rearrangement furnished the sesquiterpene arylmethylcyclopentane skeleton. The formal syntheses of herbertane-type β-herbertenol, cuparane-type enokipodins A and B were also achieved.

Pyridine-Hydrazone Ligands in Asymmetric Palladium-Catalyzed 1,4- and 1,6-Additions of Arylboronic Acids to Cyclic (Di)enones

Catalysts generated by combinations of Pd(TFA)2 and enantiomerically pure pyridine-hydrazone ligands have been applied to the 1,4-addition of arylboronic acids to β-substituted cyclic enones, building all-carbon quaternary stereocenters in high

A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Additions of Arylboronic Acids to β,β-Disubstituted Enones

A palladium(II)-functionalized covalent organic framework (Pd@TpBpy COF) constructed from 1,3,5-triformylphloroglucinol (Tp) and [2,2′-bipyridine]-5,5′-diamine (Bpy) is reported as a recyclable catalyst for conjugate additions in aqueous media. Additions

MOF-253-Pd(OAc)2: A recyclable MOF for transition-metal catalysis in water

We report palladium(ii)-functionalized MOF-253 (MOF-253-Pd(OAc)2) as a recyclable catalyst to form all-carbon quaternary centers via conjugate additions of arylboronic acids to β,β-disubstituted enones in aqueous media. We demonstrate MOF-253-Pd(OAc)2 can be reused 8 times to form ketone products in yields above 75% while maintaining its crystallinity. Additions of a range of stereoelectronically diverse arylboronic acids to a variety of β,β-disubstituted enones catalyzed by MOF-253-Pd(OAc)2 occur in modest-to-high yields (34-95%).

Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Benzylic Quaternary Centers

Palladium-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones in aqueous media is reported. Additions of a wide range of arylboronic acids to β,β-disubstituted enones occur to form ketone products bearing benzylic all-carbon quaternary centers. These reactions are promoted by a simple catalyst prepared from palladium trifluoracetate and 2,2′-bipyridine. The use of aqueous sodium trifluoracetate as the reaction medium significantly enhances reactivity and enables the formation of challenging bis-benzylic and ortho-substituted benzylic all-carbon quaternary centers.

Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones

Abstract The development and optimization of a palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enone conjugate acceptors is described. These reactions employ air-stable and readily-available reagents in an operationally si

Efficient formation of benzylic quaternary centers via palladium catalysis

Four's a crowd: An efficient protocol for the formation of benzylic quaternary centers via arylation of enones using a catalyst made from Pd(O 2CCF3)2 and 2,2′-bipyridine is developed. For cyclic substrates, catalyst loadi