36169-67-2

Upstream product

• 110-00-9 furan 
• 108-94-1 cyclohexanone 

Downstream Products

• 14032-66-7 5-hydroxy-2-(5H)-furanone 
• 14174-50-6 2-(cyclohex-1-en-1-yl)furan 
• 7023-45-2 dicrotyl ether 
• 235787-72-1 2-(1-azidocyclohexyl)furan 
• 235787-70-9 2-(2-furyl)cyclohexyl-N-(4-tolylsulfonyl)amine 
• 235787-77-6 1-(4-tolylsulfonyl)-1-azaspiro[5.5]undec-3-ene-2,5-dione 
• 4481-78-1 1-oxa-spiro[5.5]undecan-2-one 
• 5974-84-5 1-Oxaspiro<5.5>undec-4-ene 
• 36067-19-3 2-hydroxy-1-oxaspiro<5.5>undec-3-en-5-one 

Relevant academic research and scientific papers

Enantioconvergent Biocatalytic Redox Isomerization

Alcohol dehydrogenases can act as powerful catalysts in the preparation of optically pure γ-hydroxy-δ-lactones by means of an enantioconvergent dynamic redox isomerization of readily available Achmatowicz-type pyranones. Imitating the traditionally metal-

A convenient synthesis of 1-oxaspiro[5.5]undecane derivatives

2-Hydroxy-1-oxaspiro[5.5]undec-3-en-5-one, which is derived from 1-(2-furyl)cyclohexan-1-ol, is used in a convenient synthesis of several 1-oxaspiro[5.5]undecane derivatives.

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

CtD strategy to construct stereochemically complex and structurally diverse compounds from griseofulvin

The Complexity to Diversity (CtD) strategy, a strategy for the synthesis of stereochemically complex and structurally diverse small molecules from natural products using ring-distortion reactions, was applied in the synthesis of a 47-member compound collection from the natural product griseofulvin. A Tsuji-Trost allylation and oxa-Michael cyclization tandem reaction was used for the first time in the CtD strategy to generate complex ring fused compounds.

Visible-light-mediated achmatowicz rearrangement

Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.

Divergent approach to the polymaxenolide and pinnaic acid cores

The divergent syntheses of the spirocyclic pyran core of polymaxenolide and the spirocyclic piperidine core of pinnaic acid have been achieved. Our divergent approach takes advantage of highly efficient Achmatowicz and aza-Achmatowicz rearrangements to ge

Singlet Oxygen Oxidation of Substituted Furans to 5-Hydroxy-2(5H)-furanone

The conditions for the regiospecific singlet oxygen oxidation of various 2,4-disubstituted furans 9 to 4-substituted-2(5H)-furanones 3 are developed.The presence of a C-2 substituent (e.g., trimethylsilyl, tert-butyldimethylsilyl, or tributylstannyl) in 9 is an absolute requirement for the formation of the 4-substituted-5-hydroxy-2(5H)-furanone regioisomer 3.When the C-2 substituent is triethylsilyl (TES) or TBDMS, however, apart from 3, the corresponding 5-trialkylsiloxy derivative 11 is also isolated in a significant amount.These silyl acetals are unexpectedly stable but can be hydrolyzed back to 3 on stirring with dilute acid.The formation of silyl acetals, to our knowledge, has never been reported in the singlet oxygen oxidation of (trialkylsilyl)furan.A plausible mechanism for their formation is proposed.The presence of a catalytic amount of water in the oxidation of 2-(trialkylsilyl)-4-substituted-furans not only eliminates the formation of the silyl acetals but also speeds up the rate of the oxidation process.Moreover, the oxidation can then be carried out at 0 deg C instead of at -78 deg C.Oxidation of 2-(1-hydroxyalkyl)-4-substituted-furans in the absence of a reducing agent gives little or no sign of 2,5-disubstituted-6-hydroxy-3(2H)-pyranone 23 but instead 26 selectively.Thus, the (1-hydroxy)alkyl group can be utilized as the trialkylsilyl or trialkylstannyl group in dictating the regioselectivity in the singlet oxygen oxidation of substituted furans.

Chiral Synthesis via Organoboranes. 11. Hydroboration. 82. Asymmetric Hydroboration of 1-Heteroarylcycloalkenes with Monoisopinocampheylborane. Synthesis of trans-2-Heteroarylcycloalkyl Boronates and Derived Alcohols of Very High Enantiomeric Purity

The hydroboration of represantative 1-heteroarylcycloalkenes with monoisopinocampheylborane (IpcBH2) was investigated systematically to establish the degree of asymmetric induction during hydroboration.The hydroboration of 1-heteroarylcyclopentene with IpcBH2 at -25 deg C proceeded cleanly to afford the corresponding dialkylboranes.These dialkylboranes, upon treatment with acetaldehyde and then oxidation, afforded the corresponding trans-2-heteroarylcycloalkanols of 85-86percent ee.Similarly, 1-heteroarylcyclohexenes, upon hydroboration with IpcBH2, followed by acetaldehyde treatment and oxidation, gave the corresponding alcohols in ca. 90percent ee.The dialylboranes or alkylboronic acids derived from 1-heteroarylcyclopentenes and IpcBH2 can be recrystallized to furnish materials approaching 100percent ee.From such dialkylboranes or alkylboronic acids, the corresponding boronates of ca. 100percent ee were prepared and isolated.These proving to be highly versatile synthetic intermediates for organic synthesis.

Use of 2-Thienyl, 2-Furyl, 5-Ethyl-2-furyl, and Protonated 4-Acetylphenyl Substituents in Carbon-14 Nuclear Magnetic Resonance Chemical Shift Correlations

The application of the tool of increasing electron demand has been extended by employing increased electron-withdrawing as well as electron-donating substituents.In combination with the electron-withdrawing 4-protonated acetylphenyl substituent and the el