126087-53-4

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 591-50-4 iodobenzene 
• 100-52-7 benzaldehyde 
• 158070-09-8 Z-1-trimethylsilyl-4-trimethylsilyloxy-butene 
• 87682-77-7 (Z)-4-(trimethylsilyl)-but-3-en-1-ol 
• 107399-01-9 (Z)-4-tributylstannylbut-3-en-1-ol 
• 195720-93-5 2-phenyl-3-(p-toluenesulfonyl)-5,6-dihydro-2H-pyran 
• 936447-64-2 4-bromo-2-phenyltetrahydro-2H-pyran 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 5390-04-5 pent-1-yn-5-ol 
• 108-86-1 bromobenzene 

Downstream Products

• 4203-44-5 2-phenyltetrahydropyran 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 
• 58927-91-6 cis-5-phenyl-3-penten-1-ol 

Relevant academic research and scientific papers

The silyl-Prins reaction: A novel method for the synthesis of dihydropyrans

Reaction of 4-trimethylsilyl-3-buten-1-ols with aldehydes under mild Lewis acid conditions gives substituted dihydropyrans in excellent yields and with good stereocontrol.

Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins

We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.

Green chemistry: Solvent- and metal-free Prins cyclization. Application to sequential reactions

Prins cyclization between a homoallylic alcohol and an aldehyde, promoted by trimethylsilyl halide, afforded 4-halo-tetrahydropyrans with good to excellent yields. Thanks to the absence of the solvent and metal, the THP thus obtained have been implicated

An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization

A general method has been developed for the stereoselective construction of 2,6-disubstituted dihydropyrans based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with vinylstannanes. This novel methodology was applied to the enan

BiBr3-initiated tandem addition/silyl-prins reactions to 2,6-disubstituted dihydropyrans

A tandem addition/silyl-Prins reaction efficiently affords cis-2,6-disubstituted dihydropyrans (DHPs) using 5 mol % of BiBr3 in CH2Cl2. The reaction occurs between δ- triethylsilyloxyvinyltrimethylsilanes and a variety of

A facile synthesis of aryldihydropyrans using a Sonogashira-selenoetherification strategy

A high yielding and convenient synthesis of 2-aryl-2,5-dihydro-2H-pyrans is reported. Sonogashira coupling of 4-pentyn-1-ol and 5-hexyn-2-ol with a range of phenyl and naphthyl bromides affords the appropriate aryl acetylenic alcohols which then undergo r

The intramolecular silyl-modified sakurai (ISMS) reaction. Synthetic studies towards ambruticine

The ISMS reaction has been used to efficiently construct the right-hand portion 3 of the antifungal antibiotic ambruticine 1.

IMPROVED PROCEDURES FOR THE PALLADIUM-CATALYZED INTERMOLECULAR ARYLATION OF CYCLIC ALKENES

Improved procedures for the palladium-catalyzed, intermolecular, allylic crosscoupling of aryl halides and cyclic alkenes inhibit double-bond isomerization and accommodate many important functional groups.