%0 Journal Article %T Enantioselective Synthesis of Medium-Sized-Ring Lactones by Organocatalytic Michael Addition Followed by Reductively Initiated Fragmentation %+ Institut des Sciences Moléculaires de Marseille (ISM2) %A Roudier, Mylène %A Quintard, Adrien %A Rodriguez, Jean %< avec comité de lecture %@ 0947-6539 %J Chemistry - A European Journal %I Wiley-VCH Verlag %P 5709 %8 2015-07-15 %D 2015 %R 10.1002/ejoc.201500894 %K Organocatalysis %K Enantioselectivity %K Ring expansion %K Medium lactones %K Natural products %Z Chemical Sciences/Organic chemistryJournal articles %X A new strategy for the rapid synthesis of enantioenriched medium-sized-ring lactones was developed. The method combines the organocatalytic Michael addition of cycloalkane-1,3-diones to α,β-unsaturated aldehydes with a subsequent reductively initiated Claisen fragmentation, which allows access to 10- and 11-membered-ring lactones with 91 to 99%ee. %G English %L hal-01224310 %U https://hal.science/hal-01224310 %~ CNRS %~ UNIV-AMU %~ EC-MARSEILLE %~ ISM2 %~ INC-CNRS %~ ANR %~ TEST2-HALCNRS