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Stereoselective Synthesis of Tetrasubstituted Alkenes via a Cp*Co III ‐Catalyzed C−H Alkenylation/Directing Group Migration Sequence
Author(s) -
Ikemoto Hideya,
Tanaka Ryo,
Sakata Ken,
Kanai Motomu,
Yoshino Tatsuhiko,
Matsunaga Shigeki
Publication year - 2017
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.201703193
Subject(s) - moiety , stereoselectivity , catalysis , alkene , chemistry , sequence (biology) , leaving group , surface modification , group (periodic table) , acylation , stereochemistry , medicinal chemistry , organic chemistry , biochemistry
Abstract A highly atom economical and stereoselective synthesis of tetrasubstituted α,β‐unsaturated amides was achieved by a Cp*Co III ‐catalyzed C−H alkenylation/directing group migration sequence. A carbamoyl directing group, which is typically removed after C−H functionalization, worked as an internal acylating agent and migrated onto the alkene moiety of the product. The directing group migration was realized with the Cp*Co III catalyst, while a related Cp*Rh III catalyst did not promote the migration process. The product was further converted into two types of tricyclic compounds, one of which had fluorescent properties.