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Stereospecific Synthesis of Hetero[7]helicenes by Pd‐Catalyzed Double N ‐Arylation and Intramolecular O ‐Arylation
Author(s) -
Nakano Koji,
Hidehira Yuko,
Takahashi Keita,
Hiyama Tamejiro,
Nozaki Kyoko
Publication year - 2005
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.200502855
Subject(s) - helicene , enantiopure drug , intramolecular force , palladium , stereospecificity , chemistry , aniline , stereoselectivity , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , molecule
Enantioenriched aza‐ and oxa[7]helicenes are synthesized from an enantiopure biphenanthryldiol in a highly stereoselective manner. An N ‐phenylaza[7]helicene is prepared by a palladium‐catalyzed double N ‐arylation of aniline with disulfonate derivatives (see scheme, right), whereas an oxa[7]helicene is obtained by a palladium‐catalyzed intramolecular O ‐arylation of monosulfonate derivatives (see scheme, left).