4746-86-5Relevant academic research and scientific papers
Rapid, One-Step Synthesis of α-Ketoacetals via Electrophilic Etherification
Paris, Timothy J.,Schwartz, Chris,Sundall, Eric,Willand-Charnley, Rachel
, p. 14797 - 14811 (2021/10/20)
Herein, we report a rapid, one-step synthesis of α-ketoacetals via electrophilic etherification of α-alkoxy enolates and monoperoxyacetals. Methyl, primary, and secondary α-ketoacetals were obtained in 44-63% yields from tetrahydropyranyl substrates; usin
Cascade annulative π-extension for the rapid construction of carbazole based polyaromatic hydrocarbons
Banerjee, Ankush,Ghosh, Meghna,Kundu, Samrat,Maji, Modhu Sudan,Pal, Shyam Chand
supporting information, p. 5762 - 5765 (2021/06/16)
A Br?nsted acid catalyzed cascade benzannulation strategy for the one-pot synthesis of densely populated poly-aryl benzo[a]carbazole architectures is disclosed from easily affordable fundamental commodities. The efficacy of this technique was further validated via the concise synthesis of structurally unique carbazole based poly-aromatic hydrocarbons. Furthermore, the photo-physical properties of the synthesized compounds are thoroughly investigated.
The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Bronsted Acids
Zhang, Xin,Dai, Yijing,Wulff, William D.
, p. 2015 - 2018 (2018/09/18)
An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.
Rapid Construction of Complex 2-Pyrrolines through Lewis Acid-Catalyzed, Sequential Three-Component Reactions via in Situ-Generated 1-Azaallyl Cations
Schlegel, Marcel,Schneider, Christoph
supporting information, p. 3119 - 3123 (2018/05/28)
The first Sc(OTf)3-catalyzed dehydration of 2-hydroxy oxime ethers to generate benzylic stabilized 1-azaallyl cations, which are captured by 1,3-carbonyls, is described. A subsequent addition of primary amines in a sequential three-component re
Catalytic asymmetric α-iminol rearrangement: New chiral platforms
Zhang, Xin,Staples, Richard J.,Rheingold, Arnold L,Wulff, William D.
supporting information, p. 13971 - 13974 (2014/12/10)
A series of 19 different asymmetric catalysts were screened in an effort to identify the first chiral catalyst for the rearrangement of α-hydroxy imines to α-amino ketones involving a 1,2-carbon shift. Although aluminate complexes of VAPOL, VANOL, and 7,7'-tBu2VANOL were quite effective catalysts giving up to 88% ee, the ne plus ultra catalyst for this reaction was found to be a zirconium complex of VANOL which gives 97 to >99% ee for the majority of the substrates examined. An X-ray diffraction study of the catalyst reveals that the zirconium exists as a homoleptic complex with three VANOL ligands and two protonated N-methyl imidazoles.
Rhodium-catalyzed carbometalation of ynamides with organoboron reagents
Gourdet, Benoit,Smith, Donna L.,Lam, Hon Wai
scheme or table, p. 6026 - 6031 (2010/09/10)
In the presence of catalytic [Rh(cod)(MeCN)2]BF4, ynamides undergo carbometalation with boronic acids, arylboronic esters, and triarylboroxines. These reactions enable the regio- and stereocontrolled synthesis of multisubstituted ena
Carbanions with two N substituents: Nucleophilic acyl-group-transfer reagents
Bojer, Daniel,Kamps, Ina,Tian, Xin,Hepp, Alexander,Pape, Tania,Froehlich, Roland,Mitzel, Norbert W.
, p. 4176 - 4179 (2008/03/12)
(Chemical Equation Presented) Without mercury or thallium: A new umpoled nucleophilic acylation reagent is formed in the direct deprotonation of 1,3,5-trimethyl-1,3,5-triazacyclohexane with butyllithium. The carbanionic center is flanked by two amino grou
Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines
Konev,Novikov,Khlebnikov
, p. 286 - 296 (2007/10/03)
N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-π-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dimethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-π-cyclization, in the presence of acid catalysts suffer isomerization into α-fluoroimines and 1,3-disubstituted indoles.
A silver salt - iodine reagent system for the deprotection of monothioacetals and dithioacetals
Nishide, Kiyoharu,Nakamura, Daisaku,Yokota, Kouichi,Sumiya, Toshio,Node, Manabu,Ueda, Masaru,Fuji, Kaoru
, p. 393 - 404 (2007/10/03)
A new reagent (silver salt - iodine) system was developed for the deprotection of monothioacetals and dithioacetals. The reactions using this reagent system afforded the parent carbonyl compounds in moderate to quantitative yields under mild conditions. T
Reduction of α-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride (DIBAH): A Facile Preparation of α-Trialkylsiloxy Aldehydes and their Derivatives
Hayashi, Masahiko,Yoshiga, Tomoko,Nakatani, Kanako,Ono, Kazuyuki,Oguni, Nobuki
, p. 2821 - 2830 (2007/10/02)
The stepwise synthesis of α-trimethylsiloxy aldehydes and α-hydroxy aldehydes could be achieved via the reduction of α-trimethylsiloxy nitriles with diisobutylaluminium hydride (DIBAH) starting from a variety of ketones.The facile synthesis of optically active α-tert-butyldimethylsiloxy aldehydes was attained by combination of asymmetric silylcyanation of aldehydes and DIBAH reduction of optically active α-siloxy nitriles.Furthermore, in the reduction of some α-tert-butyldimethylsiloxy-β,γ-unsaturated nitriles, migration of the double bond took place to form more stable α-siloxy-α,β-unsaturated aldehydes under some reaction conditions.
