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Rhodium Enalcarbenoids: Direct Synthesis of Indoles by Rhodium(II)‐Catalyzed [4+2] Benzannulation of Pyrroles
Author(s) -
Dawande Sudam Ganpat,
Kanchupalli Vinaykumar,
Kalepu Jagadeesh,
Chennamsetti Haribabu,
Lad Bapurao Sudam,
Katukojvala Sreenivas
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201400161
Subject(s) - rhodium , chemistry , catalysis , electrophile , combinatorial chemistry , natural product , stereochemistry , organic chemistry
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.