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

Dominik Niedek; Sören M. M. Schuler; Christian Eschmann; Raffael C. Wende; Alexander Seitz; Felix Keul; Peter R. Schreiner

doi:10.1055/s-0036-1589404

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(02): 371-382
DOI: 10.1055/s-0036-1589404

paper

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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Abstract

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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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Referenzen

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