Copper-Catalyzed Intramolecular Desymmetric Aryl CO Coupling for the Enantioselective Construction of Chiral Dihydrobenzofurans and Dihydrobenzopyrans

O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad ran...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie Vol. 127; no. 30; pp. 8929 - 8932
Main Authors Yang, Wenqiang, Liu, Yangyuan, Zhang, Shasha, Cai, Qian
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.07.2015
WILEY‐VCH Verlag
Subjects
2,3‐Dihydrobenzofuran
3-Dihydrobenzofuran
Aromatic compounds
Asymmetrische Katalyse
Carbon
Catalysis
Compatibility
Construction
Desymmetrisierung
Formations
Joining
Kupfer
O-Arylierung
Strategy
Online AccessGet full text

Cover

More Information
Summary:O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad range of substrates are compatible with this CuI‐diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. O‐Heterocyclen wie chirale Dihydrobenzofurane wurden durch eine kupferkatalysierte Desymmetrisierung mit einem chiralen cyclischen 1,2‐Diaminliganden enantioselektiv hergestellt. Eine Reihe von Substraten ist mit diesem CuI‐Diamin‐Katalysesystem kompatibel und liefert die Kupplungsprodukte mit chiralen tertiären oder quartären Kohlenstoffzentren unter milden Bedingungen in hohen Ausbeuten und guten bis sehr guten Enantioselektivitäten.
Bibliography:ArticleID:ANGE201503882
istex:26AA85A9799E99CC01D9BAD87E41CEE108BA90AA
ark:/67375/WNG-F1T83LV6-1
We are grateful to the National Natural Science Foundation (Grant 21272234) for their financial support. We also thank Prof. Dr. Jinsong Liu and Yongzhi Lu from Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, for the X-ray experiments.
National Natural Science Foundation - No. 21272234
We are grateful to the National Natural Science Foundation (Grant 21272234) for their financial support. We also thank Prof. Dr. Jinsong Liu and Yongzhi Lu from Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, for the X‐ray experiments.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201503882