A catalytic and enantioselective preparation of the ()-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 -butyl ()-4-methyleneprolinate () into the -Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (), a key element in the industrial synthesis of antiviral ledipasvir.
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| http://dx.doi.org/10.3390/molecules25235644 | DOI Listing |
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