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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
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:
It is part of: Molecules, 2020, vol. 25, num. 23, p. 5644-5654
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ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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