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
收藏
页码：7249 / 7252
页数：4
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