42969-66-4

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 108-94-1 cyclohexanone 

Downstream Products

• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 1345012-81-8 (E)-3-cyclohexylidene-5-phenylpent-4-en-1-ol 
• 1345012-67-0 (3-cyclohexylidene-1-(vinyloxy)allyl)benzene 
• 1357268-87-1 1-phenyl-3-(1-((tetrahydro-2H-pyran-2-yl)oxy)cyclohexyl)prop-2-yn-1-ol 
• 1228108-22-2 (3-cyclohexylideneallyloxymethyl)benzene 

Relevant academic research and scientific papers

Zwitterionic imidazolium salt: An efficient organocatalyst for tetrahydropyranylation of alcohols

An aprotic imidazole based zwitterionic-salt, 4-(3-methylimidazolium)-butane sulfonate has been found to be an efficient organocatalyst for tetrahydropyranylation by the reaction of 3,4-dihydro-2H-pyran (DHP) and different aliphatic alcohols as well as various phenolic compounds. The notable advantages of the present method are general applicability to various alcohols, clean reaction, production of no hazardous waste, open air reaction conditions and high yields. The catalyst can be reused without the loss of significant catalytic activity.

Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand

The efficient hydroformylation of 1,1,3-trisubstituted allenes is accomplished with low loadings of a Rh catalyst supported by a BisDiazaPhos (BDP) ligand. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions m

Enantioselective construction of branched 1,3-dienyl substituted quaternary carbon stereocenters by asymmetric allenyl Claisen rearrangement

The availability of enantiomerically enriched 1,3-dienyl substituted quaternary stereocenters is highly valuable for the synthesis of complex natural compounds. Despite great advances in the area of construction of alkenyl-substituted types, a general, pr

Copper-catalyzed borylation of α-alkoxy allenes with bis(pinacolato)diboron: Efficient synthesis of 2-boryl 1,3-butadienes

Something solid to build on: 2-Boryl 1,3-butadienes with various substitution patterns were formed in good to high yields in a copper-catalyzed borylation of α-alkoxy allenes with bis(pinacolato)diboron (see scheme; Bn=benzyl, pin=pinacolate, L is an N-he

Pd-catalyzed asymmetric synthesis of N-allenyl amides and their Au-catalyzed cycloisomerizative hydroalkylation: A new route toward enantioenriched pyrrolidones

Palladium to make them, gold to cyclize them! Gold-catalyzed cycloisomerizative hydroalkylation of N-allenyl amides affords regioselectively 4-vinyl-γ-lactams. This transformation is stereospecific and takes place with a total axis-to-center chirality tra

Dual reactivity of O-α-allenyl esters under palladium(0) catalysis: From carbopalladation/allylic alkylation domino sequence to decarboxylative allenylation

In a mechanistically-oriented study, O-α-allenyl esters have been evaluated as potential substrates for Pd-catalyzed carbopalladation/allylic alkylation domino sequences and decarboxylative allenylation reactions. The domino sequence turned out to be feas

Gold(i)-catalyzed Claisen rearrangement of allenyl vinyl ethers; Synthesis of substituted 1,3-dienes

Synthesis of substituted 1,3-dienes was achieved via gold(i)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbene gold chloride catalyst (IPrAuCl) was superior in terms of activity and selectivity and afforded the 3,3-product in excellent yields. A proposed cation-π inter-action played a significant role in affecting the reaction rate.

Facile synthesis of dihaloheterocycles via electrophilic iodocyclization

An efficient and facile electrophilic iodocyclization for the synthesis of various O-, N-, and S-containing dihaloheterocycles has been developed. A wide range of the substituted propargyl alcohols having -OH, -NTs, and -SAc functional groups reacted with molecular iodine or bromoiodine at ambient temperature to produce the corresponding dihalogenated O-, N-, and S-containing five- and six-membered heterocycles in good to high yields; Under optimized solvent conditions, the reactions of various substituted but-2-yn-1-ones bearing -OH, -NTs, and -SAc functional groups at C4-position, with iodine or bromoiodine at ambient temperature afforded the corresponding 3,4-diiodo- and 3-bromo-4-iodo-substituted furans, pyrroles, and thiophenes in good to high yields. Further transformation of the resulting iodine- or bromine-containing products to polyaromatics potentially of useful as organo-material intermediates has been investigated.

Unusual regiodivergence in metal-catalysed intramolecular cyclisation of γ-allenols

Different O-heterocycles can be obtained from a common γ-allenol precursor by using Ag, Zn or Sn catalysts; the results were rationalised by molecular modelling. The Royal Society of Chemistry 2009.

Generally applicable organocatalytic tetrahydropyranylation of hydroxy functionalities with very low catalyst loading

This paper presents the first acid-free, organocatalytic tetrahydropyran and 2-methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected alcohols, and cyanohydrins. The catalytic efficiency is truly remarkably with turnover numbers of 100,000 and turnover frequencies of up to 5700 h-1 at catalyst loadings down to 0.001 mol%. The computationally supported mechanistic interpretation emphasizes the hydrogen bond assisted heterolysis of the alcohol and concomitant preferential stabilization of the oxyanion hole in the transition state. Georg Thieme Verlag Stuttgart.