74552-56-0Relevant academic research and scientific papers
Solvent Dependence of the Monomer–Dimer Equilibrium of Ketone-Substituted Triscatecholate Titanium(IV) Complexes
Kwamen, A. Carel N.,Jenniches, Judith,Oppel, Iris M.,Albrecht, Markus
supporting information, p. 10550 - 10554 (2020/07/24)
Hierarchical helicates based on ketone-substituted titanium(IV)triscatecholates show different monomer-dimer behavior depending on different solvents. The dimerization constants of a whole series of differently alkyl-substituted complexes is analyzed to show that the solvent has a very strong influence on the dimerization. Hereby, effects like solvophobicity/philicity, sterics, electronics of the substituents and weak side-chain—side-chain interactions seem to act in concert.
Cyanide-catalyzed additions of acyl phosphonates to aldehydes: A new acyl donor for benzoin-type reactions
Bausch, Cory C.,Johnson, Jeffrey S.
, p. 1207 - 1211 (2007/10/03)
Acyl phosphonates have been utilized as new acyl donors for cyanide-catalyzed benzoin-type reactions. Cyanation of acyl phosphonates, followed by a [1,2]-phosphoryl migration generates the active acyl anion intermediate. The presumed (cyano)phosphate anion reacts with a variety of aryl aldehydes to yield phosphate ester-protected, unsymmetrical benzoins in good to excellent yields. The unsymmetrical benzoin product can be obtained after deprotection of the phosphate ester with an aqueous amine solution.
Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
Pirrung, Michael C.,Shuey, Steven W.
, p. 3890 - 3897 (2007/10/02)
Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically.These compounds can be useful in light-directed synthesis and caging.The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields.Two groups, 2',3'-dimethoxybenzoin and 3',5'-dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters.These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism.An asymmetric synthesis of 3',5'-dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols.A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives.These compounds were deprotected photochemically to produce the phosphodiesters in high yield.
α-Heterosubstituted Phosphonate Carbanions. 11. Benzoins via an Acyl Anion Equivalent. Novel One-Pot Preparation of Benzofurans via Benzoins Using Hydriodic Acid
Koenigkramer, Rusty E.,Zimmer, Hans
, p. 3994 - 3998 (2007/10/02)
Diethyl 1-(trimethylsiloxy)-1-phenylmethanephosphonate carbanion 2 is introduced as a novel acyl anion equivalent.When 2 reacts with aldehydes or ketones, a 1,4 oxygen-oxygen silicon migration with subsequent loss of diethyl lithium phosphite is observed.An efficient method utilizing 2 for the preparation of otherwise difficultly obtainable substituted benzoins is presented.Also a novel one-pot method which offers a facile entry into the 2-phenylbenzofuran ring system from 2 via benzoin intermediates using hydriodic acid was developed.
