An enantiodivergent synthesis of C-alpha-methyl nipecotic acid analogues from delta-lactam derivatives obtained through a highly stereoselective cyclization strategy

作者：Banerjee Souvik; Vogel Emily R; Hinton Daniel; Sterling Michael; Masterson Douglas S^*

来源：Tetrahedron: Asymmetry , 2015, 26(21-22): 1292-1299.

DOI：10.1016/j.tetasy.2015.09.014

A stereoselective and enantiodivergent strategy for the construction of delta-lactams is described. The strategy utilizes chiral malefic 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 delta-lactams are then converted into nipecotic acid analogues using straightforward transformations. The resulting nipecotic acid analogues proved capable organocatalysts in Mannich reactions.

• 出版日期2015-12-1