22089-60-7

Upstream product

• 4218-62-6 benzyl diphenyl phosphate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 870-63-3 prenyl bromide 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 85738-96-1 E/Z-1-Brom-3-methyl-1-buten 

Downstream Products

• 27644-02-6 2,2-dimethyl-1-phenylbut-3-en-1-ol 
• 70275-04-6 C₁₈H₂₀OS 
• 123502-30-7 (E)-3-methyl-5-benzyloxy-1,3-pentadiene 
• 101376-74-3 (E)-4-(benzyloxy)-2-methylbut-2-enal 
• 296777-70-3 (3-methyl-but-2-enyl)-carbamic acid benzyl ester 
• 70238-41-4 (E)-4-(benzyloxy)-2-methylbut-2-en-1-ol 
• 103791-01-1 Z-4-benzyloxy-2-methyl-2-buten-1-al 
• 794513-02-3 ((2S,3S)-3-Benzyloxymethyl-2-methyl-oxiranyl)-methanol 
• 60066-73-1 benzyl 3,3-dimethyl-4-pentenoate 
• 214333-88-7 2-Benzyloxymethyl-3,3-dimethyl-cyclobutanone 
• 1015249-48-5 acetic acid 1-benzyloxymethyl-2-hydroxy-2-methyl-propyl ester 
• 958264-81-8 C₂₈H₅₂OSi₂ 
• 1180480-99-2 C₂₃H₄₄OSi₂ 
• 106226-14-6 C₁₂H₁₄O₂ 

Relevant academic research and scientific papers

Synthesis of functionalized 3,3,9,9-tetramethyl-4,8-diazaundecane-2,10-dione dioximes (propylene amine oximes, PnAOs)

The syntheses of several new derivatives of PnAO and their chloronitroso precursors are described. The PnAOs were prepared by an improvement of the reported general procedure. An unexpected product, an isooxalone, was formed while attempting to prepare 1-

Detection of C-Nitroso Dimer Formation by Field Desorption Mass Spectrometry

Field desorption mass spectrometry is shown to be a useful technique for observing dimer formation in C-nitroso compounds.Mixed dimer formation (RN2O2R') is shown to be readily observed by field desorption mass spectrometry.

Transition state analysis of model and enzymatic prenylation reactions

To obtain a transition state (TS) structure for an enzyme-catalyzed prenylation reaction, SN1 and SN2 model substitution reactions with dimethylallyl chloride were first studied. 13C Kinetic isotope effects (KIEs) for the model reactions were measured by a natural abundance NMR method and used to validate the computational methods that would be used in the subsequent determination of the enzymatic TS structure. Using a primary 13C KIE and a secondary 2H KIE measured via mass spectrometry, a TS structure for the enzyme-catalyzed reaction was computed; a density functional level of electronic structure theory using the mPW1N functional in combination with the 6-31+G(d) basis set was employed for those calculations. That structure has a C-O bond length of 1.69 A and a C-S bond length of 3.70 A. While the former bond length is similar to that for a nonenzymatic SN2 reaction, the latter is considerably (0.90 A) longer, indicating that the enzyme effects catalysis via an "exploded" TS structure. Copyright

Organocatalyzed Domino [3+2] Cycloaddition/Payne-Type Rearrangement using Carbon Dioxide and Epoxy Alcohols

An unprecedented organocatalytic approach towards highly substituted cyclic carbonates from tri- and tetrasubstituted oxiranes and carbon dioxide has been developed. The protocol involves the use of a simple and cheap superbase under mild, additive- and metal-free conditions towards the initial formation of a less substituted carbonate product that equilibrates to a tri- or even tetrasubstituted cyclic carbonate under thermodynamic control. The latter are conveniently trapped in situ, providing overall a new domino process for synthetically elusive heterocyclic scaffolds. Control experiments provide a rationale for the observed cascade reactions, which demonstrate similarity to the well-known Payne rearrangement of epoxy alcohols.

A dehydrogenative diels-alder reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone

An efficient dehydrogenative Diels-Alder (DHDA) reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) has been developed under mild conditions, leading to a series of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivity.

Selectivity in the addition reactions of organometallic reagents to aziridine-2-carboxaldehydes: The effects of protecting groups and substitution patterns

Good to excellent stereoselectivity has been found in the addition reactions of Grignard and organozinc reagents to N-protected aziridine-2-carboxaldehydes. Specifically, high syn selectivity was obtained with benzyl-protected cis, tert-butyloxycarbonyl-protected trans, and tosyl-protected 2,3-disubstituted aziridine-2-carboxaldehydes. Furthermore, rate and selectivity effects of ring substituents, temperature, solvent, and Lewis acid and base modifiers were studied. The diastereomeric preference of addition is dominated by the substrate aziridines' substitution pattern and especially the electronic character and conformational preferences of the nitrogen protecting groups. To help rationalize the observed stereochemical outcomes, conformational and electronic structural analyses of a series of model systems representing the various substitution patterns have been explored by density functional calculations at the B3LYP/6-31G* level of theory with the SM8 solvation model to account for solvent effects. Grignard and bear it: Good to excellent stereoselectivity is reported for the addition reactions of Grignard and organozinc reagents to N-protected aziridine-2-carboxaldehydes (see scheme). High syn selectivity was obtained with benzyl-protected cis, tert-butyloxycarbonyl-protected trans, and tosyl-protected 2,3-disubstituted aziridine-2-carboxaldehydes. Copyright

Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.

Encapsulated molecular catalysts in polysiloxane gels: Ruthenium cluster-catalyzed isomerization of alkenes

Novel ruthenium-encapsulating polysiloxane gels are prepared by treatment of polymethylhydrosiloxane with diols in the presence of (μ3, η2,η3,η5-acenaphthylene)Ru 3(CO)7, and act as reusable catalysts in the isomerization of alkenes without leakage of the catalyst species. The Royal Society of Chemistry.

Metal-catalyzed silylene insertions of allylic ethers: Stereoselective formation of chiral allylic silanes

Silylene insertion into allylic ethers occurs suprafacially to provide enantioenriched allylic silanes and disilanes. Silylene insertion to a variety of protected allylic alcohols utilizing silver- and copper-mediated conditions proved to be a general method for allylic silane formation. Allylic disilanes reacted similarly to allylic silanes, undergoing both annulation and allylation reactions. Copyright

Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.