395065-67-5Relevant academic research and scientific papers
Iridium-catalyzed direct asymmetric vinylogous allylic alkylation
Shi, Chang-Yun,Xiao, Jun-Zhao,Yin, Liang
, p. 11957 - 11960 (2018/11/02)
The catalytic asymmetric vinylogous allylic alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.
Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: Asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps
Palucki, Michael,Um, Joann M.,Yasuda, Nobuyoshi,Conlon, David A.,Tsay, Fuh-Rong,Hartner, Frederick W.,Hsiao, Yi,Marcune, Benjamin,Karady, Sandor,Hughes, David L.,Dormer, Peter G.,Reider, Paul J.
, p. 5508 - 5516 (2007/10/03)
An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)-cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.
