Enantioselective synthesis

Schöllkopf Bis-lactim Amino Acid Synthesis

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Alanine and valine are converted to a cyclic dioxopiperazine followed by double methylation to form the bis-lactim. Deprotonation and highly diastereoselective alkylation opposite the bulky isopropyl group completes the reaction. Acidic hydrolysis leads to formation of the alkylated amino acid.

U. Schöllkopf, Tetrahedron, 1983, 39, 2085–2091.