In Situ Anionic Shielding for Regioselective Metalation: Directed  peri  and Iterative Metalation Routes to Polyfunctionalized 7‐Azaindoles | Zendy

Schneider Cédric | Zendy; David Emilie | Zendy; Toutov Anton A. | Zendy; Snieckus Victor | Zendy

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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.

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