Development of a new and practical route to chiral 3, 4-disubstituted cyclopentanones: asymmetric alkylation and intramolecular cyclopropanation as key CC bond- …
M Palucki, JM Um, N Yasuda, DA Conlon…
文献索引：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. Journal of Organic Chemistry, 2002 , vol. 67, # 16 p. 5508 - 5516
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 ...
