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Domino Cyclodimerization of Indole‐Derived Donor–Acceptor Cyclopropanes: One‐Step Construction of the Pentaleno[1,6‐ a , b ]indole Skeleton
Author(s) -
Ivanova Olga A.,
Budynina Ekaterina M.,
Chagarovskiy Alexey O.,
Rakhmankulov Eduard R.,
Trushkov Igor V.,
Semeykin Alexander V.,
Shimanovskii Nikolay L.,
Melnikov Mikhail Ya.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101687
Subject(s) - indole test , stereocenter , domino , stereoselectivity , chemistry , acceptor , stereochemistry , combinatorial chemistry , order (exchange) , organic chemistry , catalysis , enantioselective synthesis , physics , business , finance , condensed matter physics
The fellowship of the rings : The previously undiscovered ability of indole‐derived donor–acceptor cyclopropanes to involve four reaction centers simultaneously was revealed by their domino cyclodimerization (see scheme). This SnCl 4 ‐induced reaction affords bisindole products with the pentaleno[1,6‐ a , b ]indole framework. In the course of this process, two new rings, three CC bonds, and four stereocenters are formed with exceptional chemo‐, regio‐, and stereoselectivity.