28968-16-3Relevant academic research and scientific papers
Palladium-Catalyzed Enantioselective Thiocarbonylation of Styrenes
Wang, Xihong,Wang, Bing,Yin, Xuemei,Yu, Wangzhi,Liao, Yang,Ye, Jialin,Wang, Min,Hu, Lianrui,Liao, Jian
, p. 12264 - 12270 (2019/08/01)
A highly enantioselective thiocarbonylation of styrenes with CO and thiols has been achieved by Pd catalysis, providing highly enantioenriched thioesters in good to excellent yields. Key to the successful execution of this reaction is the use of a chiral sulfoxide-(P-dialkyl)-phosphine (SOP) ligands. This thiocarbonylation proceeds smoothly under mild reaction conditions (1 atm CO and 0 °C) and displays broad substrate scope. Also demonstrated is that this transformation can be conducted using surrogates of CO, greatly increasing the safety aspects of running the reaction. The generality and utility of the method is manifested by its application to the synthetic transformations of thioester products and the direct acylation of cysteine-containing dipeptides. A primary mechanism was investigated and a plausible catalytic cycle was proposed.
Chiral bronsted acid from a cationic gold(I) complex: Catalytic enantioselective protonation of silyl enol ethers of ketones
Cheon, Cheol Hong,Kanno, Osamu,Toste, F. Dean
supporting information; experimental part, p. 13248 - 13251 (2011/10/10)
A chiral Bronsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furthermore, the application of this Bronsted acid was extended to the first Bronsted acid-catalyzed enantioselective protonation reaction of silyl enol ethers of acyclic substrates, regardless of their E/Z ratio.
Catalytic asymmetric cross-couplings of racemic α-bromoketones with arylzinc reagents
Lundin, Pamela M.,Esquivias, Jorge,Fu, Gregory C.
supporting information; experimental part, p. 154 - 156 (2009/04/07)
(Chemical Equation Presented) Nickel box: The first catalytic asymmetric method for cross-coupling arylzinc reagents with α-bromoketones has been developed (see scheme). This stereoconvergent carbon-carbon bond-forming process occurs under unusually mild conditions and without activators, thereby allowing the generation of potentially labile tertiary stereocenters.
A Crystallisation Technique for the Enantiomer Resolution of Conglomerates: (+/-)-4-Methoxyphenyl 1-Phenylethyl Ketone
Chandrasekhar, Sosale,Ravindranath, Mukkamala
, p. 210 (2007/10/03)
The sorting of crystals of (+/-)-4-methoxyphenyl 1-phenylethyl ketone into its enantiomers is facilitated by crystallisation in a cellur grid made of filter paper.
'PREFERENTIAL SPONTANEOUS RESOLUTION' OF p-ANISYL α-METHYLBENZYL KETONE
Chandrasekhar, Sosale,Ravindranath, Mukkamala
, p. 6207 - 6208 (2007/10/02)
The title compound has been obtained in optically-active form without using any chiral influence, by 'preferential spontaneous resolution'.
