TY - JOUR
T1 - Amino Acid-Derived trans-N-Chloroformylimidazolidinones
T2 - Scalable, Stereoselective Synthesis, Structure, and Utility
AU - Amer, Mostafa Mahmoud
AU - Abas, Hossay
AU - Leonard, Daniel J.
AU - Ward, John W.
AU - Clayden, Jonathan
PY - 2019/6/7
Y1 - 2019/6/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85066933003&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b00727
DO - 10.1021/acs.joc.9b00727
M3 - Article (Academic Journal)
C2 - 31090419
AN - SCOPUS:85066933003
SN - 0022-3263
VL - 84
SP - 7199
EP - 7206
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 11
ER -