期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 11, 页码 7199-7206出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00727
关键词
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资金
- Presidential Leadership Program of Egypt
- European Research Council
- EPSRC
- Engineering and Physical Sciences Research Council [EP/L011999/1] Funding Source: researchfish
- EPSRC [EP/L011999/1] Funding Source: UKRI
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.
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