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A new synthetic route to highly enantioenriched 3-substituted-2,3-dihydro-1H-isoindol-1-ones

✍ Scribed by Eric Deniau; Dieter Enders; Axel Couture; Pierre Grandclaudon

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
164 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

A concise and efficient synthesis of highly enantioenriched 3-alkyl and 3-aryl-2,3-dihydro-1H-isoindolinones is reported. The key step relies on the diastereoselective reduction of the N-acylhydrazonium salts generated by acidic treatment of hemiaminal precursors bearing the (S)-2-methoxymethylpyrrolidin-1-yl (SMP) auxiliary.

📜 SIMILAR VOLUMES

Hydriodic Acid-Mediated Cyclization of α
Hydriodic Acid-Mediated Cyclization of α-Substituted Secondary 2-Ethenylbenzamides: Synthesis of 2-Substituted 2,3-Dihydro-3,3-dimethyl-1H-isoindol-1-ones and 3,3-Disubstituted (E)-1-(Arylimino)-1,3-dihydroisobenzofurans
✍ Kazuhiro Kobayashi; Seiki Fujita; Daisuke Nakai; Shogo Fukumoto; Shuhei Fukamach 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 German ⚖ 168 KB 👁 1 views

## Abstract A new and facile method for the preparation of 2‐substituted 2,3‐dihydro‐3,3‐dimethyl‐1__H__‐isoindol‐1‐ones **3** and 3,3‐disubstituted (__E__)‐1‐(arylimino)‐1,3‐dihydroisobenzofurans **6** has been developed. Thus, treatment of __N__‐alkyl(or aryl)‐2‐(1‐methylethen‐1‐yl)benzamides **2