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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).