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Indium‐Catalyzed Cycloisomerization of ω‐Alkynyl‐β‐ketoesters into Six‐ to Fifteen‐Membered Rings
Author(s) -
Tsuji Hayato,
Yamagata Kenichi,
Itoh Yoshimitsu,
Endo Kohei,
Nakamura Masaharu,
Nakamura Eiichi
Publication year - 2007
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.200702928
Subject(s) - cycloisomerization , indium , catalysis , ring (chemistry) , chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
Many different sizes of rings available : Heating ω‐alkynyl‐β‐ketoesters in the presence of In(NTf 2 ) 3 (Tf=trifluoromethanesulfonyl) produces six‐ to fifteen‐membered ring products in good yields. The reaction features low catalyst loading and moderately dilute conditions, and the formation of medium‐sized rings is sometimes faster than that for the corresponding six‐membered rings. A synthesis of (±)‐muscone is also reported.