130444-79-0

Upstream product

• 108-95-2 phenol 
• 90-02-8 salicylaldehyde 
• 100-42-5 styrene 
• 40473-50-5 2-(hydroxy(phenyl)methyl)phenol 
• 938068-90-7 (±)-4-phenylchroman-2-ol 
• 61198-52-5 3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one 
• 92496-19-0 4-Phenyl-4H-1-benzopyran 
• 58530-41-9 2,4-Diphenyl-2H-benzopyran 
• 98-87-3 benzylidene dichloride 
• 35822-60-7 (phenylmethylene)bis(oxy)dibenzene 
• 124313-16-2 2<α-(isopropylthio)benzyl>phenol 
• 89466-08-0 2-hydroxyphenyl boronic acid 
• 94-41-7 benzalacetophenone 

Relevant academic research and scientific papers

Hetero Diels-Alder reaction of olefin with o-quinone methides generated using (±)-binolphosphoric acid for the stereoselective synthesis of 2,4-diarylbenzopyrans: Application to the formal synthesis of myristinin B/C

Hetero Diels-Alder reaction of olefin with o-quinone methides (o-QMs) generated using (±)-binolphosphoric acid was developed for the stereoselective synthesis of 2,4-diarylbenzopyrans. The method thus developed was utilized in the formal synthesis of myri

Catalytic asymmetric synthesis of chiral phenols in ethanol with recyclable rhodium catalyst

A general method to access diverse chiral phenols by rhodium-catalyzed asymmetric conjugate arylation using hydroxylated arylboronic acids in ethanol was developed. Recycling of the rhodium catalyst by flash chromatography on silica gel was feasible in this system. The synthetic utility of the strategy was demonstrated by efficient synthesis of chiral drug tolterodine.

Multicomponent Condensation Reactions via ortho-Quinone Methides

Iron(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo Diels - Alder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy(phenyl)methyl)phenols to access the desired ortho-quinone methide in a Diels - Alder condensation. The two-component condensation also afforded the corresponding benzopyran products in yields up to 97%. Taken together, the two- and three-component strategies using ortho-quinone methide intermediates provide efficient access to benzopyrans in good yields and selectivities.

Heteroatom-Guided, Palladium-Catalyzed, Site-Selective C-H Arylation of 4H-Chromenes: Diastereoselective Assembly of the Core Structure of Myristinin B through Dual C-H Functionalization

A highly site-selective, heteroatom-guided, palladium-catalyzed direct arylation of 4H-chromenes is reported. The C-H functionalization is driven not only by the substituents and structure of the substrate but also by the coupling partner being used. The diastereoselective assembly of the core structure of Myristinin B has been achieved by using a dual C-H functionalization strategy for regioselective direct arylation.

Gold-catalyzed oxa-povarov reactions for the synthesis of highly substituted dihydrobenzopyrans from diaryloxymethylarenes and olefins

Oxa-Povarov reactions involving readily available diaryloxymethylarenes and aryl-substituted alkenes are reported. Their [4+2] cycloadditions were efficiently catalyzed by IPrAuSbF6 (IPr=1,3-bis(diisopropylphenyl) imidazol-2-ylidene) with high diastereoselectivity. Product analysis revealed that the reactions likely proceed by a stepwise ionic mechanism, because both E- and Z-configured β-methylstyrene gave the same cycloadducts in the same proportions.

Novel Generation of o-Quinone Methides on the Basis of Lewis Acid Catalyzed 1,4-Dethiolation of o-(1-(Alkylthio)alkyl)phenols

The treatment of o-(1-(alkylthio)alkyl)phenols with Lewis acid resulted in the formation of o-quinone methides by the novel 1,4-dethiolation process, which, being activated with Lewis acid, reacted in situ with various dienophiles in the manner of Diels-Alder reaction in high efficiency. o-Quinone allide, provided from o-(1-(alkylthio)allyl)phenol, also behaved as heterodienes.