335314-64-2Relevant academic research and scientific papers
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.
