Amino Acid-Derived trans-N‑Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility

N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by “self-regeneration of stereochemistry” methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presen...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (11), p.7199-7206
Main Authors: Amer, Mostafa Mahmoud, Abas, Hossay, Leonard, Daniel J, Ward, John W, Clayden, Jonathan
Format: Article
Language:English
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Summary:N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by “self-regeneration of stereochemistry” methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presence of pyridine may be made fully diastereoselective for the trans-N-chloroformylimidazolidinones, and we detail the conformational features of the products. We show that despite the presence of the electrophilic carbamoyl chloride function the products show remarkable stability and may be deprotonated to form enolates with useful reactivity for the synthesis of amino acid derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00727