55629-83-9

Upstream product

• 945844-27-9 C₁₁H₁₂O₂ 
• 70672-97-8 (1-methoxybut-3-yn-1-yl)benzene 
• 80783-99-9 N-methoxy-N-methylcinnamamide 
• 107-30-2 chloromethyl methyl ether 
• 945844-28-0 1-methoxy-4-phenylbut-3-yn-2-one 
• 536-74-3 phenylacetylene 
• 67-56-1 methanol 

Relevant academic research and scientific papers

CAN-mediated tandem 5-exo-cyclisation of tertiary aminocyclopropanes: Novel accelerative effect of an N-benzyl group for oxidative ring-opening

Treatment of tertiary cyclopropylamines with cerium(IV) ammonium nitrate (CAN) gave ring-opened ketones and/or bicyclic secondary amines via an oxidative cyclopropane cleavage followed by a hydrogen abstraction or 5-exo radical cyclization: an N-benzyl gr

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.

Gold-catalyzed oxidative rearrangement of homopropargylic ether via oxonium ylide

Synthetically useful α,β-unsaturated carbonyl compounds were obtained from gold-catalyzed oxidative rearrangement of homopropargylic ether under mild reaction conditions. Gold carbenoid and oxonium ylide are proposed as key intermediates.

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.