Synthesis of Enantioenriched Phthalide and Isoindolinone Derivatives from 2-Formylbenzoic Acid

This manuscript is dedicated to Prof. Dieter Enders on the occasion of his 70^th birthday and for his seminal contributions to organic chemistry.

Abstract

Transformations of 2-formylbenzoic acid provide direct access to a series of heterocyclic organic compounds such as phthalides and isoindolinones. Here, we use (+)-cinchonine as a catalyst in conjunction with nonafluoro-tert-butanol as a hydrogen-bond donor to afford enantiomerically enriched acylated 3-hydroxyphthalides with up to 99% yield and 90% ee through dynamic kinetic resolution. Moreover, various 3-alkoxyphthalides as well as 2-alkyl-3-hydroxy-1-isoindolinones were synthesized from 2-formylbenzoic acid.

Keywords

acylation - chiral auxiliary - cinchona alkaloids - dynamic kinetic resolution - organocatalysis

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