A highly diastereoselective synthesis of isoindolinone-centered Meyers' tetracyclic lactams. Application to the asymmetric synthesis of 3-alkylisoindolinones

作者：Agouridas Vangelis; Capet Frederic; Couture Axel^*; Deniau Eric; Grandclaudon Pierre

来源：Tetrahedron: Asymmetry , 2011, 22(13): 1441-1447.

DOI：10.1016/j.tetasy.2011.07.020

A new methodology for the asymmetric synthesis of C-3 alkylated isoindolinones has been developed through a novel extension of Meyers' lactamisation. The key polycyclic lactam precursor was prepared in high yield and high diastereoselectivity by a two step sequence involving phthalic anhydride and aminoprolinol. Metallation/alkylation followed by hydride reduction of the transient N-acylhydrazonium species and ultimate removal of the chiral auxiliary without a loss of stereochemical integrity completed the synthesis of the target compounds.

• 出版日期2011-7-15