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Versatile precursor to ruthenium‐bis(phosphine) hydrogenation catalysts
Author(s) -
Akotsi Okwado M.,
Metera Kim,
Reid R.D.,
McDonald Robert,
Bergens Steven H.
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<514::aid-chir38>3.0.co;2-#
Subject(s) - chemistry , ruthenium , phosphine , catalysis , noyori asymmetric hydrogenation , organic chemistry , combinatorial chemistry
The known complex trans ‐RuCl 2 (NBD)Py 2 ( 1, NBD is norbornadiene, Py is pyridine) reacts with either (R)‐BINAP ((R)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl), (S;S)‐Chiraphos ((2S;3S‐(−)‐2,3‐bis(diphenylphosphino)butane), (S;S)‐Skewphos ((2S;4S)‐(−)‐2,4‐bis(diphenylphosphino)pentane), (R)‐(S)‐Josiphos ((R)‐(−)‐1‐[(S)‐2‐(diphenylphosphino)ferrocenyl]ethyl‐dicyclohexylphosphine), (R;R)‐Norphos ((2R;3R)‐(−)‐2,3‐bis(diphenylphosphino)bicyclo[2.2.1]hept‐5‐ene), or (R;R)‐Me‐DUPHOS ((−)‐1,2‐bis((2R;5R)‐2,5‐dimethylphospholano)benzene) to generate in high yields the crystalline complexes trans ‐RuCl 2 (P‐P*)Py 2 (P‐P* is the corresponding chiral bis(phosphine)). The complexes trans ‐RuCl 2 (P‐P*)Py 2 are active enantioselective hydrogenation catalysts for ketoesters and noncarboxylic olefins in the presence of small amounts of HBF 4 (aq.). They are active for hydrogenation of carboxylic substrates in the presence of Et 3 N. Reaction of trans ‐RuCl 2 (P‐P*)Py 2 with ( rac )‐1,2‐diphenylethylene‐diamine (N‐N*, either enantiomer) forms in good yields the corresponding compounds trans ‐RuCl 2 (P‐P*)(N‐N*). Representative hydrogenations with these catalysts are presented. Chirality 12:514–522, 2000. © 2000 Wiley‐Liss, Inc.