Enantioselective Synthesis of Medium-Sized-Ring Lactones by Organocatalytic Michael Addition Followed by Reductively Initiated Fragmentation

Mylène Roudier (1) , Adrien Quintard (1) , Jean Rodriguez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

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.

Keywords: Organocatalysis; Enantioselectivity; Ring expansion; Medium lactones; Natural products

Domains: Organic chemistry

Mylène Roudier, Adrien Quintard, Jean Rodriguez. Enantioselective Synthesis of Medium-Sized-Ring Lactones by Organocatalytic Michael Addition Followed by Reductively Initiated Fragmentation. Chemistry - A European Journal, 2015, pp.5709. ⟨10.1002/ejoc.201500894⟩. ⟨hal-01224310⟩