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Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions
Author(s) -
Tahara Yuki,
Matsubara Riku,
Mitake Akihito,
Sato Tatsuki,
Kanyiva Kyalo Stephen,
Shibata Takanori
Publication year - 2016
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.201511876
Subject(s) - enantioselective synthesis , racemization , intermolecular force , catalysis , chemistry , computational chemistry , sulfide , combinatorial chemistry , molecule , organic chemistry
Abstract The first catalytic and highly enantioselective synthesis of tribenzothiepin derivatives was achieved. Two types of intermolecular cycloadditions using either diphenyl‐sulfide‐tethered diynes or 2‐phenyl sulfanylbenzene‐tethered diynes with a monoalkyne successfully gave chiral multisubstituted tribenzothiepins in good to excellent ee values under mild conditions. The inversion energy of this saddle‐shaped molecule was calculated by measurement of the racemization rate of chiral tribenzothiepins using the Eyring kinetic equation under heating conditions. The present protocol could also be used to prepare a chiral tribenzoselenepin.