945844-28-0

Upstream product

• 38870-89-2 Methoxyacetyl chloride 
• 536-74-3 phenylacetylene 
• 132289-57-7 (N-methyl-N-methoxy)methoxyacetamide 
• 132960-13-5 N-methoxy-N-methyl-3-phenyl-2-propynamide 
• 107-30-2 chloromethyl methyl ether 
• 98-88-4 benzoyl chloride 

Downstream Products

• 945844-27-9 C₁₁H₁₂O₂ 
• 55629-83-9 (3E)-1-methoxy-4-phenyl-3-buten-2-one 

Relevant academic research and scientific papers

Enantioselective Cyanosilylation of Alkynyl Ketones Catalyzed by Combined Systems Consisting of Chiral Ruthenium(II) Complex and Lithium Phenoxide

Asymmetric cyanosilylation of alkynyl ketones with the catalyst systems consisting of amino acid/2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP)/ruthenium(II) complex and lithium phenoxide (Ru?Li cat.) was studied. The reaction was conducted in tert-butyl methyl ether (TBME) at ?78 °C with a substrate-to-catalyst molar ratio (S/C) as high as 2000. A series of simple and functionalized ketones was converted into the alkynyl tertiary cyanohydrin derivatives in up to 99% ee. Appropriate selection of an amino-acid ligand of the catalyst according to the substrate structure was crucially important to achieve high enantioselectivity and a wide scope of substrates. Transformation of the chiral cyanohydrin product into a functionalized lactone was also examined. (Figure presented.).

Highly efficient synthesis of functionalized α-oxyketones: Via Weinreb amides homologation with α-oxygenated organolithiums

An efficient, chemoselective homologation of Weinreb amides to the corresponding variously substituted α-oxyketones has been developed via the addition of lithiated α-oxygenated species. This one-step, experimentally easy, high yielding protocol is amenable not only for accessing simple α-oxyketones but also for more complex substituted ones ranging from primary and secondary alkyl-type to aromatic ones. Full delivery of the stereochemical information contained in the starting materials is observed through both the employment of enantioenriched Weinreb amides and optically active organolithium species.

Cationic rhodium(I)/bisphosphane complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones

We have determined that hydrogenated cationic Rh(I)/bisphosphane complexes are highly active catalysts for the isomerization of secondary propargylic alcohols to α,β-enones. A kinetic resolution of secondary propargylic alcohols proceeded with moderate selectivity with [Rh((R)-BINA-P)]OTf as a catalyst. Mechanistic studies revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways. The isomerization of propargylic diol derivatives was also investigated, which revealed that 1,4-diketones, furans, and α,β-enones were obtained from 2-butyn-1,4-diol, 1-methoxy-2-butyn-4-ol, and 1-acetoxy-2-butyn-4-ol derivatives, respectively. Furthermore, chemoselectivity of the isomerization of an acetylenic diol was investigated, and preferential oxidation of a propargylic hydroxy group was observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Microwave assisted intramolecular wittig reaction: A facile method for the synthesis of conjugated acetylenes

A rapid and efficient synthesis of acetylenic compounds by the microwave assisted intramolecular Wittig reaction of β-oxo-alkylidene-triphenylphosphoranes is reported.