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.
Verendel
J Johan
JJ
Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, BMC. S-751 23, Uppsala, Sweden.
Andersson
Pher G
PG
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