Abstract
A series of N-unsubstituted esters of aziridine-2-carboxylic acid has been obtained by transesterification in basic medium using primary, secondary, and tertiary alcohols. Methods of transesterification using various bases (K2CO3, ROLi, t-BuOK) have been compared. Transesterification with lithium alcoholates also affords the possibility of obtaining esters of N-substituted aziridine-2-carboxylic acids. Transesterification of chiral esters proceeds with retention of the configuration of the chiral center.
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Shtrumfs, B., Chernyak, D., Kums, I. et al. Unnatural Amino Acids. 2. Simple Method of Obtaining Esters of Aziridine-2-carboxylic Acids by a Transesterification Reaction. Chemistry of Heterocyclic Compounds 40, 725–733 (2004). https://doi.org/10.1023/B:COHC.0000040767.96090.cc
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DOI: https://doi.org/10.1023/B:COHC.0000040767.96090.cc