92862-87-8

Upstream product

• 6330-12-7 3-(4-methylphenyl)cyclohex-2-enone 
• 75-16-1 methylmagnesium bromide 
• 75-24-1 trimethylaluminum 
• 30182-67-3 1,3-Cyclohexanedione 
• 23074-59-1 3-isobutoxycyclohex-2-en-1-one 
• 917-54-4 methyllithium 
• 94853-56-2 3-methyl-3-(4-methylphenyl)-pent-4-enal 
• 882745-48-4 6-methyl-6-p-tolyl-octa-1,7-dien-4-ol 
• 882745-49-5 5-methyl-5-p-tolyl-cyclohex-3-enol 
• 1193-18-6 3-methylcyclohexen-2-one 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 882745-50-8 5-(4-methylphenyl)-5-methylcyclohex-3-enone 
• 108-88-3 toluene 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 882876-36-0 1,4',5-trimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl 
• 882745-53-1 1-(4-methylphenyl)-1-methyl-3-methylenecyclohexane 

Relevant academic research and scientific papers

Catalytic enantioselective total synthesis of (?)-ar-Tenuifolene

First catalytic asymmetric total synthesis of aromatic sesquiterpene, (?)-ar-teunifolene (1) is featured (3 steps, 75% overall yields) from commercially available 3-methyl cyclohex-2-enone 16. The enantioenriched 3,3-disubstituted cyclohexanone 11 is obtained from Pd(II)-catalyzed enantioselective (p-tolyl)boronic acid addition to 3-methyl cyclohex-2-enone 16 in 90% ee, which is found to be the key intermediate. A diastereoselective methyllithium addition of this enantioenriched product followed by dehydration completes straightforward access to (?)-ar-teunifolene (1).

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

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

Palladium-catalyzed asymmetric quaternary stereocenter formation

An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters

The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst

Cationic Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones: Construction of quaternary carbon centers

Cationic Pd(II)-catalyzed addition of arylboronic acids to β,β-disubstituted enones in high yields was developed. This method provided an efficient method for the construction of quaternary carbon centers, and only 0.5 mol % of Pd(II) catalyst was needed.

First synthesis of (±)-tenuifolene and ar-tenuifolene

First total synthesis of the sesquiterpenes (±)-tenuifolene and (±)-ar-tenuifolene, isolated from the essential oil of the East African sandalwood tree Osyris tenuifolia, has been accomplished.