An Approach to 2,3-Diaminosuccinic Acid Derivatives—Synthesis of 2-Thioxo-1,3-Imidazolidines by a Mannich Reaction
Dariusz Cież A B , Justyna Kalinowska-Tłuścik A and Jakub Marchewka A
+ Author Affiliations
- Author Affiliations
A Faculty of Chemistry, Jagiellonian University, 30-060 Kraków, Poland.
B Corresponding author. Email: ciez@chemia.uj.edu.pl
Australian Journal of Chemistry 65(4) 333-342 https://doi.org/10.1071/CH11463
Submitted: 7 December 2011 Accepted: 30 January 2012 Published: 20 March 2012
Abstract
The article deals with a new synthesis of 2-thioxo-1,3-imidazolidine derivatives, masked 2,3-diaminosuccinic acids. The described procedure leads to the designed products by an intermolecular Mannich reaction between aldimine (ethyl iminoacetate) and enolates derived from 2-isothiocyanatocarboxylic esters. The prepared heterocyclic products having two stereogenic centers can be easily separated into cis- and trans- diastereoisomers. The reactivity of titanium(iv), lithium, and potassium enolates and the influence of ester groups on the yields and diastereoselectivities of the Mannich reactions are discussed.
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