Chemistry and Biochemistry
Mathematics and Natural Sciences
A stereoselective and enantiodivergent strategy for the construction of δ-lactams is described. The strategy utilizes chiral malonic esters prepared from enantiomerically enriched mono esters of disubstituted malonic acid. A cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. The resulting δ-lactams are then converted into nipecotic acid analogues using straightforward transformations. The resulting nipecotic acid analogues proved capable organocatalysts in Mannich reactions.
(2015). An Enantiodivergent Synthesis of Cα-Methyl Nipecotic Acid Analogues From Î´-Lactam Derivatives Obtained Through a Highly Stereoselective Cyclization Strategy. Tetrahedron Asymmetry, 26(21-22), 1292-1299.
Available at: https://aquila.usm.edu/fac_pubs/18645