105515-33-1Relevant articles and documents
Strong acid-catalyzed electrophilic ring expansion of oxetanes and sulfoxonium ylides
Xie, Wenlai,Xu, Jiaxi,Yuan, Wenhao
, (2021)
A strong protic acid-catalyzed electrophilic ring expansion of oxetanes into trans-2,3-disubstituted tetrahydrofuran derivatives using sulfoxonium ylides has been developed. This reaction produces functionalized trans-2,3-disubstituted tetrahydrofuran derivatives stereospecifically by using safe and stable sulfoxonium ylides without metal catalysts and the protection of inert gas.
Highly selective methanesulfonic acid-catalyzed 1,3-isomerization of allylic alcohols
Leleti, Rajender Reddy,Hu, Bin,Prashad, Mahavir,Repi?, Oljan
, p. 8505 - 8507 (2007)
Secondary and tertiary allylic alcohols undergo 1,3-isomerization smoothly in the presence of methanesulfonic acid under simple and efficient conditions to afford selectively the corresponding primary E-allylic alcohols in excellent yields.
Heterotelechelic Polymers by Ring-Opening Metathesis and Regioselective Chain Transfer
Liu, Peng,Yasir, Mohammad,Ruggi, Albert,Kilbinger, Andreas F. M.
, p. 914 - 917 (2018)
Heterotelechelic polymers were synthesized by a kinetic telechelic ring-opening metathesis polymerization method relying on the regioselective cross-metathesis of the propagating Grubbs’ first-generation catalyst with cinnamyl alcohol derivatives. This procedure allowed the synthesis of hetero-bis-end-functional polymers in a one-pot setup. The molecular weight of the polymers could be controlled by varying the ratio between cinnamyl alcohol derivatives and monomer. The end functional groups can be changed using different aromatically substituted cinnamyl alcohol derivatives. Different monomers were investigated and the presence of the functional groups was shown by NMR spectroscopy and MALDI-ToF mass spectrometry. Labeling experiments with dyes were conducted to demonstrate the orthogonal addressability of both chain ends of the heterotelechelic polymers obtained.
(1-(Dimethylamino)-2-(diphenylphosphino)ethane)(η 3-1-arylallyl)palladiuin tetrafluoroborates. Preparation, isomeric equilibria, and correlations of NMR chemical shifts with hammett substituent constants
Malet, Ramo?n,Moreno-Man?as, Marcial,Parella, Teodor,Pleixats, Roser
, p. 758 - 763 (1996)
13C NMR differences of chemical shifts (δX - δH) of allyl carbon atoms in a series of trans-(1-(diphenylphospnino)-2-(dimethylamino)ethane)(η 3-1-arylallyl)palladium tetrafluoroborates, X ranging from NO2 to OMe, correlate very well with σ Hammett constants for C-1 and with σ+ for C-3, this carbon atom being in a irons relationship with the positively charged nitrogen atom.
Macrocycles All Aflutter: Substitution at an Allylic Center Reveals the Conformational Dynamics of [13]-Macrodilactones
Rutledge, Kelli M.,Hamlin, Trevor A.,Baldisseri, Donna M.,Bickelhaupt, F. Matthias,Peczuh, Mark W.
, p. 2623 - 2633 (2017)
The shapes adopted by large-ring macrocyclic compounds play a role in their reactivity and their ability to be bound by biomolecules. We investigated the synthesis, conformational analysis, and properties of a specific family of [13]-macrodilactones as models of natural-product macrocycles. The features of our macrodilactones enabled us to study the relationship between stereogenic centers and planar chirality through the modular synthesis of new members of this family of macrocycles. Here we report on insights gained from a new [13]-macrodilactone that is substituted at a position adjacent to the alkene in the molecule. Analysis of the compound, in comparison to an α-substituted regioisomer, by using X-ray crystallography, NMR coupling constants, and reaction-product characterization in concert with computational chemistry, revealed that the alkene unit is dynamic. That is, the data support a model in which the alkene in our [13]-macrodilactones oscillates between two conformations. A difference in reactivity of one conformation compared to the other leads to manifestation of this dynamic behavior. The results underscore the local conformational dynamics observed in some natural-product macrocycles, which could have implications for biomolecule binding.
Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole
Chen, Yi,Gao, Lu,Song, Xuanyi,Song, Zhenlei
supporting information, p. 124 - 128 (2021/01/13)
A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.
Method for synthesizing photoactive bromohydrin compound
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Paragraph 0040-0044, (2021/07/21)
The invention discloses a method for synthesizing a photoactive bromohydrin compound, which comprises the following steps: reacting cinnamyl alcohol as shown in a formula I, benzamide bromide as shown in a formula II, a quinine derivative, L-camphorsulfonic acid and water in a first organic solvent to obtain the bromohydrin compound as shown in a formula III. According to the method, raw materials are easy to synthesize, reaction conditions are mild, operation is easy and convenient, the yield reaches up to 47%-87%, enantioselectivity can generally reach 80% or above, and the highest point can even reach 95%.
