Chiral Fidelity in the Diastereoselective and Enantiospecific Synthesis of Indenes from Axially Chiral Benzylidene Cyclanes

Dominique Mouysset (1) , Cyril Tessonnier (1) , Aura Tintaru (1) , Frederic Dumur (1) , Marion Jean (2) , Nicolas Vanthuyne (2) , Michèle P. Bertrand (1) , Didier Siri (1) , Malek Nechab (1)

1 ICR - Institut de Chimie Radicalaire
2 ISM2 - Institut des Sciences Moléculaires de Marseille

Enantioenriched indenes were reached through a chirality conversion strategy using original axially chiral benzylidene cyclanes. Good to high remote diastereocon-trol and excellent enantiocontrol were observed in this cascade involving copper-catalyzed homologation of terminal alkynes, in situ allenoate formation and Alder-ene cyclization.

Domaines: Chimie

Dominique Mouysset, Cyril Tessonnier, Aura Tintaru, Frederic Dumur, Marion Jean, et al.. Chiral Fidelity in the Diastereoselective and Enantiospecific Synthesis of Indenes from Axially Chiral Benzylidene Cyclanes. Chemistry - A European Journal, 2017, 23 (35), pp.8375 - 8379. ⟨10.1002/chem.201701501⟩. ⟨hal-01682754⟩