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Intramolecular Consecutive Dehydro‐Diels–Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality
Author(s) -
Shibata Takanori,
Sekine Ayato,
Mitake Akihito,
Kanyiva Kyalo Stephen
Publication year - 2018
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.201810174
Subject(s) - enantioselective synthesis , rhodium , moiety , intramolecular force , chirality (physics) , catalysis , axial chirality , diels–alder reaction , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Consecutive thermal and metal‐catalyzed dehydro‐Diels–Alder (DDA) reactions of sulfur‐tethered tetraynes, possessing a 1,3‐diyne moiety, proceeded efficiently, and axial chirality was achieved for the resulting dibenzothiophenyl moieties. Chiral‐rhodium catalysis realized a highly enantioselective synthesis, and transformations into bis(benzocarbazole) derivatives were also achieved.