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Selective Isomerization of a Terminal Olefin Catalyzed by a Ruthenium Complex: The Synthesis of Indoles through Ring‐Closing Metathesis
Author(s) -
Arisawa Mitsuhiro,
Terada Yukiyoshi,
Nakagawa Masako,
Nishida Atsushi
Publication year - 2002
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.200290031
Subject(s) - isomerization , ruthenium , ring closing metathesis , catalysis , acyclic diene metathesis , chemistry , carbene , metathesis , olefin fiber , medicinal chemistry , styrene , ring (chemistry) , photochemistry , organic chemistry , copolymer , polymerization , polymer
A ruthenium complex , generated from the Grubbs carbene catalyst with vinyloxytrimethylsilane, catalyzed the isomerization of terminal alkenes RCH 2 CHCH 2 to internal alkenes RCHCHCH 3 . Application of this olefin isomerization to 2‐( N ‐allylamino)styrene gave the corresponding enamines, which were converted into indoles by a standard ring‐closing metathesis, see scheme (Ts=tosyl).