Synthesis 2017; 49(02): 371-382
DOI: 10.1055/s-0036-1589404
paper
© Georg Thieme Verlag Stuttgart · New York

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

Dominik Niedek
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
,
Sören M. M. Schuler
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
,
Christian Eschmann
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
,
Raffael C. Wende
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
,
Alexander Seitz
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
,
Felix Keul
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
,
Peter R. Schreiner*
Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   eMail: prs@uni-giessen.de
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Publikationsverlauf

Received: 28. Juli 2016

Accepted after revision: 05. Oktober 2016

Publikationsdatum:
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.

Supporting Information

 
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