An Enantioselective Synthesis of Spirobilactams through Copper-Catalyzed Intramolecular Double N-Arylation and Phase Separation

被引：30

作者：

Liu, Jianguang ^{[1
]}

Tian, Yingying ^{[1
]}

Shi, Jialing ^{[2
]}

Zhang, Shasha ^{[1
]}

Cai, Qian ^{[1
]}

机构：

[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Guangzhou 510530, Guangdong, Peoples R China

[2] Hunan Normal Univ, Coll Chem & Chem Engn, Changsha 410081, Hunan, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 37期

关键词：

asymmetric catalysis; copper; N-arylation; phase separation; spirobilactams; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; ENANTIOMERIC EXCESS; NATURAL-PRODUCTS; QUATERNARY STEREOCENTERS; PREBIOTIC CONDITIONS; 2+2+2 CYCLOADDITION; CHIRAL DIPHOSPHINE; BUILDING-BLOCKS; 3+2 ANNULATION;

D O I：

10.1002/anie.201504589

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Spirobicyclic structures are versatile building blocks for functional chiral molecules. An enantioselective synthesis of chiral spirobilactams via a copper-catalyzed double N-arylation was developed. Amplification of solution ee by insitu precipitation of the racemate was observed with this method and enantioenriched spirobilactams were obtained with excellent ee values through simple solid-solution phase separation.

引用

页码：10917 / 10920

页数：4

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