Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Stereoselective Synthesis of Tetrasubstituted Alkenes via a Cp*CoIII-Catalyzed C−H Alkenylation/Directing Group Migration Sequence

Stereoselective Synthesis of Tetrasubstituted Alkenes via a Cp*CoIII-Catalyzed C−H Alkenylation/Directing Group Migration Sequence
Hideya Ikemoto, Ken Sakata, Ryo Tanaka, Motomu Kanai, Tatsuhiko Yoshino, Shigeki Matsunaga
A highly atom economical and stereoselective synthesis of tetrasubstituted α,β-unsaturated amides was achieved by a Cp*CoIII-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*CoIII catalyst, while a related Cp*RhIII catalyst did not promote the migration process. The product was further converted into two types of tricyclic compounds, one of which had fluorescent properties. Tetrasubstituted alkenes were stereoselectively synthesized by a Cp*CoIII-catalyzed C−H alkenylation/directing group migration sequence, within which a carbamoyl functional group operates as a directing group and an internal acylating agent. A fluorescent spirocyclic molecule was generated from the resulting alkene.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703193

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