Catalytic Enantioselective Synthesis of Chiral Tetraphenylenes: Consecutive Inter‐ and Intramolecular Cycloadditions of Two Triynes | Zendy

Shibata Takanori | Zendy; Chiba Tatsuya | Zendy; Hirashima Hiroyuki | Zendy; Ueno Yasunori | Zendy; Endo Kohei | Zendy

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Catalytic Enantioselective Synthesis of Chiral Tetraphenylenes: Consecutive Inter‐ and Intramolecular Cycloadditions of Two Triynes

Author(s) -

Shibata Takanori,

Chiba Tatsuya,

Hirashima Hiroyuki,

Ueno Yasunori,

Endo Kohei

Publication year - 2009

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.200903715

Subject(s) - enantioselective synthesis , moiety , intramolecular force , cationic polymerization , stereochemistry , chemistry , catalysis , ligand (biochemistry) , combinatorial chemistry , sequence (biology) , organic chemistry , receptor , biochemistry

Triynes having a phenylene‐bridged 1,5‐diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh–ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO 2 Me) 2 , O).

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