López Barallobre, BlancaBartra Sanmartí, MartíBerenguer, RamonAriza Piquer, XavierGarcía Gómez, JordiGómez, RobertoTorralvo Martín, Héctor2020-12-022020-12-022020-11-301420-3049https://hdl.handle.net/2445/172477A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline derivatives are versatile starting materials often used in medicinal chemistry. In particular, we have transformed tert-butyl (S)-4-methyleneprolinate (12) into the N-Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (1), a key element in the industrial synthesis of antiviral ledipasvir.11 p.application/pdfengcc-by (c) López Barallobre, Blanca et al., 2020http://creativecommons.org/licenses/by/3.0/esCatàlisiSíntesi de fàrmacsCatalysisDrug synthesisinfo:eu-repo/semantics/article7049802020-12-02info:eu-repo/semantics/openAccess33266105