885316-13-2Relevant academic research and scientific papers
Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters
Greenhalgh, Mark D.,Laina-Martín, Víctor,Neyyappadath, Rifahath M.,Qu, Shen,Smith, Andrew D.,Smith, Samuel M.
, p. 16572 - 16578 (2020/09/09)
A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.
Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters: Synthesis of (S)-Flutriafol
Chang, Chiung-An,Uang, Tsung-Ying,Jian, Jia-Hong,Zhou, Meng-Yi,Chen, Ming-Liang,Kuo, Ting-Shen,Wu, Ping-Yu,Wu, Hsyueh-Liang
supporting information, p. 3381 - 3390 (2018/08/06)
An enantioselective addition of arylboronic acids and α-ketoesters promoted by a Rhodium(I)-chiral diene catalyst is reported. The transformation proceeds regioselectively in the presence of as low as 0.5 mol% of the catalyst generated in situ from a Rhod
Enantioselective synthesis of quaternary stereogenic centers through catalytic asymmetric addition of dimethylzinc to α-ketoesters with chiral cis-cyclopropane-based amide alcohol as ligand
Zheng, Bing,Hou, Shicong,Li, Zhiyuan,Guo, Hongchao,Zhong, Jiangchun,Wang, Min
experimental part, p. 2125 - 2129 (2010/03/01)
A new amino alcohol with a chiral cyclopropane backbone has been developed and used in the catalytic asymmetric diethylzinc addition to various types of α-ketoesters. This cyclopropane-based chiral amino alcohol shows moderate enantioselectivity in the ad
