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

Michael Palucki, Joann M. Um, Nobuyoshi Yasuda, David A. Conlon, Fuh Rong Tsay, Frederick W. Hartner, Yi Hsiao, Benjamin Marcune, Sandor Karady, David L. Hughes, Peter G. Dormer, Paul J. Reider

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)5508-5516
Number of pages9
JournalJournal of Organic Chemistry
Volume67
Issue number16
DOIs
StatePublished - Aug 9 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Palucki, M., Um, J. M., Yasuda, N., Conlon, D. A., Tsay, F. R., Hartner, F. W., Hsiao, Y., Marcune, B., Karady, S., Hughes, D. L., Dormer, P. G., & Reider, P. J. (2002). 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. Journal of Organic Chemistry, 67(16), 5508-5516. https://doi.org/10.1021/jo025890a