Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 16, Pages 4076-4080Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201400161
Keywords
annulation; carbenes; diazo compounds; heterocycles; rhodium
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Funding
- IISER Bhopal
- Department of Science and Technology
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Disclosed herein is the design of an unprecedented electrophilic rhodium enalcarbenoid which results from rhodium(II)-catalyzed decomposition of a new class of enaldiazo compounds. The synthetic utility of these enalcarbenoids has been successfully demonstrated in the first transition-metal-catalyzed [4+2] benzannulation of pyrroles, thus leading to substituted indoles. The new benzannulation has been applied to the efficient synthesis of the natural product leiocarpone as well as a potent adipocyte fatty-acid binding protein inhibitor.
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