Rhodium-catalyzed domino enantioselective synthesis of bicyclo[2.2.2]lactones

Boyer, A. and Lautens, M. (2011) Rhodium-catalyzed domino enantioselective synthesis of bicyclo[2.2.2]lactones. Angewandte Chemie (International Edition), 50(32), pp. 7346-7349. (doi: 10.1002/anie.201101773)

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Publisher's URL: http://dx.doi.org/10.1002/anie.201101773


Once, twice, three times a catalyst! A novel domino rhodium(I)-catalyzed asymmetric transformation of substituted oxabicyclic alkenes into bicyclo[2.2.2]lactones proceeded with good yields (up to 78 %) and excellent stereoselectivity (>97 % ee; see scheme; cod=1,5-cyclooctadiene, Tf=trifluoromethanesulfonyl). Mechanistic investigations suggest that this process proceeds by rhodium-catalyzed asymmetric ring opening, allylic alcohol isomerization and oxid

Item Type:Articles
Glasgow Author(s) Enlighten ID:Boyer, Dr Alistair
Authors: Boyer, A., and Lautens, M.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie (International Edition)
Journal Abbr.:Angew Chem Int Ed Engl
ISSN (Online):1521-3773
Published Online:22 June 2011

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