Development of pinene-derived N,P ligands and their utility in catalytic asymmetric hydrogenation.
New diastereomeric N,P-ligands, derived from the natural product (+)-alpha-pinene, have been synthesized and evaluated in iridium-catalyzed asymmetric hydrogenation. The ligands are tetrahydroquinoline derivatives synthesized directly from commercially available alpha-pinene utilizing resolution or recrystallization to separate diastereomers. In reduction of a range of different trisubstituted alkenes the catalysts express very different activities ranging from no activity to high activity. One of the catalysts gives good ee values for some substrates.
Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, BMC. S-751 23, Uppsala, Sweden.
J Johan
JJ
Verendel
Pher G
PG
Andersson
D000081008:Bicyclic Monoterpenes; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D000081008:Bicyclic Monoterpenes; D008024:Ligands; D039821:Monoterpenes; D006859:Hydrogen; C005451:alpha-pinene