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In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7‐Azaindoles
Author(s) -
Schneider Cédric,
David Emilie,
Toutov Anton A.,
Snieckus Victor
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108016
Subject(s) - metalation , regioselectivity , chemistry , trimethylsilyl , ring (chemistry) , combinatorial chemistry , in situ , total synthesis , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Strolling the ring : A general regioselective directed peri (C4)‐metalation route to 1 through an in situ N‐anionic protection of C2 is reported. The azaindoles may be elaborated by directed ortho metalation (D o M) and Suzuki coupling to more complex heterocyclic systems. An iterative ring‐walk D o M sequence furnishes the exhaustively substituted 2 . DMG=directed metalation group, TMEDA= N , N , N ′, N ′‐tetramethylethylenediamine, TMS=trimethylsilyl.