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Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline

Author:
Davies, Stephen G., Fletcher, Ai M., Linsdall, Sean M., Roberts, Paul M., Thomson, James E.
Source:
Organic letters 2018 v.20 no.13 pp. 4135-4139
ISSN:
1523-7052
Subject:
chemical reactions, diastereomers, esters, ions
Abstract:
Two synthetic routes have been developed for the asymmetric syntheses of (2R,3S)- and (2S,3S)-3-hydroxyproline. The key synthetic step in each of these strategies is the conversion of protected α,δ-dihydroxy-β-amino esters (either 2,3-anti- or 2,3-syn-configured) into β,δ-dihydroxy-α-amino esters (protected forms thereof), via the intermediacy of the corresponding aziridinium ions. The products of these stereospecific rearrangements were then cyclized and deprotected to afford (2R,3S)-3-hydroxyproline and (2S,3S)-3-hydroxyproline as single diastereoisomers (>99:1 dr) in >26% overall yield.
Agid:
6084253