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Synthesis 2017; 49(02): 371-382
DOI: 10.1055/s-0036-1589404
DOI: 10.1055/s-0036-1589404
paper
Synthesis of Enantioenriched Phthalide and Isoindolinone Derivatives from 2-Formylbenzoic Acid
Further Information
Publication History
Received: 28 July 2016
Accepted after revision: 05 October 2016
Publication Date:
03 November 2016 (online)
This manuscript is dedicated to Prof. Dieter Enders on the occasion of his 70th 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 - organocatalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589404.
- Supporting Information
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