ECM - École Centrale de Marseille : UMR7313 (Pôle de l'étoile - Technopole de Château-Gombert - 38 rue Frédéric Joliot-Curie - 13013 Marseille - France)
Abstract : Enantiopure tetrasubstituted skipped diynes were readily synthesized from N-protected amino esters upon addition of lithium TMS-acetylide which was found to be desymmetrizing through one-pot selective TMS-cleavage. The deprotection of the TMS group was realized through a one-pot silicon atom attack by the liberated methoxide, which was diastereoselective due to a conformational favorable chelate.
https://hal-amu.archives-ouvertes.fr/hal-01460404 Contributor : Didier GigmesConnect in order to contact the contributor Submitted on : Tuesday, February 7, 2017 - 4:39:15 PM Last modification on : Tuesday, December 14, 2021 - 8:42:06 AM
Malek Nechab, Nicolas Vanthuyne. Synthesis of Enantiopure Tertiary Skipped Diynes via One-Pot Desymmetrizing TMS-Cleavage. Organic Letters, American Chemical Society, 2012, 14 (15), pp.3974--3977. ⟨10.1021/ol3017462⟩. ⟨hal-01460404⟩