Use of ferrocenyl ligands in catalytic enantioselective hydrogenation

• Main Authors: DRAUZ, KARLHEINZ, KNOCHEL, PAUL, ALMENA PEREA, JUAN JOSE DR, KLEMENT, INGO DR
• Format: Patent
• Language: English; French; German
• Published: 29.12.1999
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

Verwendung der Liganden und Komplexe der allgemeinen Formel I bzw. II zur katalytischen enantioselektiven Hydrierung. Enantiomerically enriched bis-phosphinyl-ferrocene ligands (I) or their metal complexes (II) are used as catalysts in the enantioselective, homogeneous catalytic hydrogenation of carbon-carbon or carbon-nitrogen double bonds. The use of enantiomerically enriched bis-phosphinyl-ferrocene ligands of formula (I) or their metal complexes of formula (II) (or salts of (I) or (II)) is claimed in the enantioselective, homogeneous catalytic hydrogenation of C=C or C=N double bonds. R1-R3 = (i) H, NR6R7 or SR6; (ii) alkyl, alkoxy, 2-8C alkoxyalkoxy or 1-8C acyloxy (all optionally substituted by one or more of halo and Q'); (iii) cycloalkyl (optionally substituted by one or more of Q, halo and Q'; and optionally having one or more T in the ring), e.g. piperidinyl, pyrrolidinyl, tetrahydrofuranyl or morpholinyl; or (iv) aryl, 6-18C aralkyl, 5-18C heteroaryl or 6-18C heteroaralkyl (e.g. phenyl, naphthyl, anthryl, benzyl, phenylethyl, furyl, pyrrolyl, pyridyl, furfuryl, pyrrolylmethyl, pyridylmethyl, furylethyl, pyrrolylethyl or pyridylethyl), all optionally substituted by one or more of Q, halo and Q'; or CR1R2 = 3-7C carbocycle (optionally substituted by one or more of Q, halo and Q'; and optionally having one or more ring T); Q = alkyl, 1-8C acyl, alkoxy or 2-8C alkoxyalkoxy (all optionally substituted by one or more of halo and Q'); Q' = group containing N, O, P or S; T = heteroatom such as N, O, P or S; R4 = (i) alkyl, aryl (e.g. phenyl, naphthyl, 2,2'-biphenylyl or anthryl) or 1-pyrrolyl (all optionally substituted by one or more of Q''); or (ii) cycloalkyl (optionally substituted by one or more of Q'', halo and Q'; and optionally having one or more ring T); Q'' = as Q but not optionally substituted acyl; R5 = H or -B-X-Z; or R5 + R5 = 2-4C n-alkylene bridge linking the two cyclopentadiene rings; B = C(R8)2, NR8, O, S or Si(R8)2; X = spacer such as 1,4'-biphenyl (sic), 1,2-ethylene, 1,3-propylene or polyethylene glycol-(2-10); Z = polymer residue, bonded via a functional group such as O, NH, COO, CONH, CH=CH, NHCONH, OCONH or NHCOO; R6, R7 = H, Q or as R1-R3 (iii) or (iv); or NR6R7 = 3-7C carbocycle (optionally substituted by one or more of Q, halo and Q'; and optionally having one or more ring T) (sic); R8 = H or alkyl; M = atom or ion of a Group VIII metal, e.g. Co, Ni, Rh, Ru, Ir, Pd, Re or Pt; unless specified otherwise alkyl moieties have 1-8C, cycloalkyl moieties 3-7C and aryl moieties 6-18C.