By Ojima I.
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Extra resources for Applications II. Transition Metal Compounds in Organic Synthesis 1
65 With this catalytic system, the hydrogenation of tert-butyl methyl ketone provides the chiral alcohol with 94% ee. Isopropyl methyl ketone and n-butyl methyl ketone are also reduced into chiral alcohols with 85% ee and 75% ee, respectively. The cyclohexyl methyl ketone is hydrogenated by the PennPhos–Rh system with 92% ee. 295 The Ru catalyst also provides a good ee (85%) for the hydrogenation of cyclohexyl methyl ketone. A racemic 2-isopropylcyclohexanone has been hydrogenated with a ternary chiral Ru catalyst consisting of RuCl2[(S)-BINAP](DMF)n, (R,R)-DPEN, and KOH.
BINAP, MeO–BIPHEP,280 BDPP281 and Me–CnrPHOS,62c are efficient for this transformation (Table 17). (vi) Diketones Several chiral Ru complexes have been applied successfully for the asymmetric hydrogenation of -, -, and -diketones. ) References Ru[(S)-MeO-BIPHEP]Br2 Ru[(S)- BINAP]Br2 Ru[(S,S)-BDPP]Br2 Ru[(S,S)-iPr-CnrPhos]Br2 50 50 100 100 MeOH, Rt, 30 atm H2 MeOH, Rt, 30 atm H2 MeOH, Rt, 30 atm H2 MeOH, 80 C, 80 atm H2 98 (S) 96 (S) 94 (S) 97 (S) 280 280 281 62c C–H Bond Formation by Asymmetric and Stereoselective Hydrogenation Table 18 Asymmetric hydrogenation of -diketones Ligand R R1 S/C ratio Reaction condition (R)-BINAP (R)-BIPHEMP (S,S)-BDPP (S,S)-iPr-CnrPhos (S,S)-Cy-BPE-4 40 (S,S)-iPr-CnrPhos 35 39 (R)-BINAP (S)-BINAP 35 (R)-3 (S)-difluorphos Me Me Me Me Me Me iPr Ph Ph ClCH2 Ph Ph Ph CF3 Me Me Me Me Me Me iPr Ph Ph ClCH2 Me Me Ph CF3 2,000 2,000 1,700 50 100 1,000 50 200 200 314 200 200 100 MeOH, Rt, 72 atm H2 EtOH, 50 C, 100 atm H2 MeOH, 80 C, 80 atm H2 MeOH, 80 C, 70 atm H2 MeOH, 80 C, 80 atm H2 MeOH, 80 C, 100 atm H2 MeOH, 80 C, 70 atm H2 EtOH, 50 C, 50 atm H2 EtOH, 50 C, 50 atm H2 MeOH, 105 C, 85 atm H2 MeOH, Rt, 72 atm H2 EtOH, 50 C, 50 atm H2 MeOH, 50 C, 1,500 psi H2 MeOH, 50 C, 50 bar H2 Percent de (anti vs.
I) Aromatic ketones Enantioselective hydrogenation of simple aromatic ketones has been studied with some chiral Rh, Ir, and Ru catalysts (Table 19). The DIOP–Rh290 and the DBPP–Rh291,291a complexes with a tertiary amine have been used in catalyzing the hydrogenation of acetophenone and moderate ee (80% and 87%, respectively) have been achieved. 65 The additives 2,6-lutidine and KBr are very important for achieving the high selectivity, although the mechanism has not been fully understood. A BINAP–Ir(I)-aminophosphine system292 and trans-[RuCl2(BINAP)(1,4-diamine)]/tBuOK combined catalyst293 have been found to be effective for hydrogenation of some cyclic aromatic ketones.