Stereospecific Synthesis of Hetero[7]helicenes by Pd‐Catalyzed Double  N ‐Arylation and Intramolecular  O ‐Arylation | Zendy

Nakano Koji | Zendy; Hidehira Yuko | Zendy; Takahashi Keita | Zendy; Hiyama Tamejiro | Zendy; Nozaki Kyoko | Zendy

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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).

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