One-Pot Synthesis, Crystallization and Deracemization of Isoindolinones from Achiral Reactants

被引：8

作者：

Steendam, Rene R. E. ^{[1
]}

Kulka, Michael W. ^{[1
]}

Meekes, Hugo ^{[1
]}

van Enckevort, Willem J. P. ^{[1
]}

Raap, Jan ^{[2
]}

Vlieg, Elias ^{[1
]}

Rutjes, Floris P. J. T. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 AJ Nijmegen, Netherlands

[2] Leiden Univ, Leiden Inst Chem, NL-2333 CC Leiden, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 33期

关键词：

Chirality; Heterocycles; Chiral resolution; Synthesis design; Multicomponent reactions; SPONTANEOUS RESOLUTION; AUTOCATALYSIS; GENERATION; EMERGENCE;

D O I：

10.1002/ejoc.201501191

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis, crystallization, and complete solid-state deracemization of isoindolinones was realized in one pot simply by grinding achiral reaction components in a suitable solvent with an achiral catalyst. Previously, this concept was applied to a reversible reaction, but herein we showed that it could also be used in combination with reactions in which product formation is irreversible. A controlled final configuration of the product was obtained by using small amounts of chiral additives or seed crystals of the product.

引用

页码：7249 / 7252

页数：4

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