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Title: | An enantioselective approach to 4-Substituted Proline Scaffolds: synthesis of (S)-5-(Tert-Butoxy Carbonyl)-5-Azaspiro[2.4]heptane-6-Carboxylic acid |
Author: | López Barallobre, Blanca Bartra Sanmartí, Martí Berenguer, Ramon Ariza Piquer, Xavier García Gómez, Jordi Gómez, Roberto Torralvo Martín, Héctor |
Keywords: | Catàlisi Síntesi de fàrmacs Catalysis Drug synthesis |
Issue Date: | 30-Nov-2020 |
Publisher: | MDPI |
Abstract: | A 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. |
Note: | Reproducció del document publicat a: https://doi.org/10.3390/molecules25235644 |
It is part of: | Molecules, 2020, vol. 25, num. 23, p. 5644-5654 |
URI: | http://hdl.handle.net/2445/172477 |
Related resource: | https://doi.org/10.3390/molecules25235644 |
ISSN: | 1420-3049 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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