CH Functionalization/Asymmetric Michael Addition Cascade Enabled by Relay Catalysis: Metal Carbenoid Used for CC Bond Formation

A combination of either ruthenium(II) or rhodium(II) complexes and quinine‐derived squaramide enables 3‐diazooxindoles, indoles, and nitroalkenes to undergo highly efficient asymmetric three‐component reactions, thus affording optically active 3,3′‐bis(indole)s through a consecutive CC bond‐forming...

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Published inAngewandte Chemie International Edition Vol. 53; no. 40; pp. 10763 - 10767
Main Authors Chen, Dian-Feng, Zhao, Feng, Hu, Yue, Gong, Liu-Zhu
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 26.09.2014
WILEY‐VCH Verlag
Wiley
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Summary:A combination of either ruthenium(II) or rhodium(II) complexes and quinine‐derived squaramide enables 3‐diazooxindoles, indoles, and nitroalkenes to undergo highly efficient asymmetric three‐component reactions, thus affording optically active 3,3′‐bis(indole)s through a consecutive CC bond‐forming sequence, which turned out to be applicable to the facile total synthesis of (−)‐folicanthine. Square deal: A combination of either ruthenium(II) or rhodium(II) complexes and quinine‐derived squaramide enables 3‐diazooxindoles, indole, and nitroalkenes to undergo a highly efficient asymmetric three‐component reaction. Based on this metal/organo relay catalysis, a total synthesis of (−)‐folicanthine was accomplished in seven steps with 14.5 % overall yield.
Bibliography:Ministry of Education
CAS
istex:41646B0DBC5915BD9ED56E07BE12C95C32163E17
We are grateful for financial support from the NSFC (21232007), MOST (973 project 2010CB833300), the Ministry of Education, and CAS.
NSFC - No. 21232007
ArticleID:ANIE201406098
ark:/67375/WNG-ZNZRMGKK-2
MOST - No. 2010CB833300
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201406098