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Ring‐Closing Metathesis of Ene‐Ynamide: Application to the Synthesis of Medium‐Sized Cyclic Dienamide
Author(s) -
Wakamatsu Hideaki,
Sakagami Maiko,
Hanata Miyuki,
Takeshita Mitsuhiro,
Mori Miwako
Publication year - 2010
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200900035
Subject(s) - chemistry , moiety , ene reaction , metathesis , yield (engineering) , substituent , carbene , salt metathesis reaction , toluene , ruthenium , ring closing metathesis , ring (chemistry) , organic chemistry , ethylene , catalysis , materials science , metallurgy , polymerization , polymer
Summary: Ring‐closing metathesis (RCM) of ene‐ynamide, which could be applied to the synthesis of various heterocycles containing 7‐ and 8‐membered rings, was investigated. Ene‐ynamides are easily synthesized by the known method. When a toluene solution of ene‐ynamide was stirred in the presence of a catalytic amount of second‐generation ruthenium carbene complex 1 under an ethylene atmosphere, RCM proceeded smoothly to provide a heterocyclic compound having a diene moiety in good to high yield. A substituent of the ynamide moiety affected the yield of the cyclized product.