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Abstract: A highly stereoselective approach to 1,3,4,5- and 1,3,3′,4,5-polysubstituted 2-oxopiperazines is reported. The method is based on the synthetic elaboration of naturally occurring amino acids to obtain enantiomerically enriched C-5 substituted oxopiperazines, which are further functionalized at C-3 via enolate formation and reaction with electrophiles. Notably, the two nitrogens of the ring can be orthogonally protected. [Copyright &y& Elsevier]

Examines the stereocontrolled addition of allylmetal reagents to α-imino esters. Synthesis of chiral tetrahydroquinoline derivatives; Preparation of multigram scale for glycine binding site; Allylation reaction of efficient stereodifferentiation process; Illustration on Heck-type cyclization reaction for trisubstituted double bond derivatives.