Ruthenium-catalyzed reactions of 1-cyclopropyl-2-propyn-1-ols with anilines and water via allenylidene intermediates: selective preparation of tri- and tetrasubstituted conjugated enynes.
Ruthenium-catalyzed efficient preparation of the conjugated enynes can be carried out in the reactions of 1-cyclopropyl-2-propyn-1-ols with nitrogen- and oxygen-centered nucleophiles such as anilines and water in the presence of a catalytic amount of sulfur-bridged diruthenium complexes. The use of such complexes as catalysts realizes the completely stereoselective preparation of tri- and tetrasubstituted conjugated enynes, where ruthenium-allenylidene complexes work as key intermediates. The direct attack of nucleophiles on a cyclopropane ring connected to an allenylidene ligand is a key step to obtain the enynes stereoselectively.
Yamauchi
Yoshihiro
Y
Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo 113-8656, Japan.
Onodera
Gen
G
Sakata
Ken
K
Yuki
Masahiro
M
Miyake
Yoshihiro
Y
Uemura
Sakae
S
Nishibayashi
Yoshiaki
Y
D000814:Aniline Compounds / Q000737:chemistry*; D001592:Benzyl Alcohols / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry
C520934:1-cyclopropyl-1-phenyl-2-propyn-1-ol; D000814:Aniline Compounds; D001592:Benzyl Alcohols; D003521:Cyclopropanes; D009942:Organometallic Compounds; D014867:Water; C023650:aniline