CH Functionalization/Asymmetric Michael Addition Cascade Enabled by Relay Catalysis: Metal Carbenoid Used for CC 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 CC bond‐forming...
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Published in | Angewandte Chemie International Edition Vol. 53; no. 40; pp. 10763 - 10767 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
26.09.2014
WILEY‐VCH Verlag Wiley |
Subjects | |
Online Access | Get full text |
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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 CC 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. |
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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 |