An enantiodivergent synthesis of Cα-methyl nipecotic acid analogues from δ-lactam derivatives obtained through a highly stereoselective cyclization strategy

Add time:08/31/2019    Source:sciencedirect.com

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.

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