Asymmetric hydrogenation of cyclic ketimines catalyzed by iridium(I)-Complexes of BCPM and Its Analog

Synlett

Volumn 1995, Issue 7, 1995, Pages 748-750

  Morimoto, T ^a   Nakajima, N ^a   Achiwa, K ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

asymmetric hydrogenation; catalyst; imine; iridium complex; pyrrolidinebisphosphine

Indexed keywords

EID: 8644269866     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5072     Document Type: Article

References (44)

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42. A typical procedure for the asymmetric hydrogenation of imines is as follows: A mixture of chloro(l, 5-cyclooctadiene)iridium(I) dimer, [Ir(COD)Cl]2 (1.6 mg, 2.5 x 103 mmol), bisphosphine ligand (6.0 x 10-3mmol) in a mixed solvent of degassed benzene and methanol (1:1) (2.0 ml) was stirred for 15 min under an argon atmosphere. A solution of tetrabutylammonium iodide (3.7 mg, 1.0 x 10-2 mmol) or bismuth (III) iodide (1.9 mg, 3.3 x 103 mmol) in a mixed solvent of benzene and methanol (1:1) (0.5 ml) was added to the mixture, and the whole was stirred for another 15 min. This catalyst solution together with imine (0.5 mmol) was placed in an autoclave (100 ml), pressurized with hydrogen to 100 atm after several exchange with hydrogen, and stirred under the conditions (temp, and time) shown in Table. Conversion was determined by GLC (column: SE 30 or PEG 20M) and ee was measured by HPLC (column: Chiralcel OJ or Chiralpack AS). 5: Chiralcel OJ; hexane : i-PrOH (IPA) = 300:1; flow rate, 0.5 ml/min; detection, 254-nm light; ts 40 min, ts. 56 min. 7 (after converting to its JV-acetyl derivative): Chiralcel OJ; hexane : IPA = 300:1; flow rate, 0.5 ml/min; detection, 254-nm light; t(.) 37 min, f(+) 45 min. 9 (after converting to its N-acetyl derivative): Chiralpack AS ; hexane : IPA = 20:1; flow rate, 1.5 ml/min; detection, 235-nm light; ts 73 min, tR 97 min. lla, b (after converting to their JV-acetyl derivatives): Chiralpack AS; hexane : IPA = 20:1; flow rate, 1.0 ml/min; detection, 254-nm light; /R 30 min, ts 38 min (11a), ?R 34 min, ts 56 min (lib). The absolute configurations of 5, 9, lla, b were determined by measuring their optical rotation values and referring to the reported ones [See Park, K. J. Prakt. Chem. 1912, 86, 287; Achiwa, K. Heterocycles 1977, 8, 247; ref. 2c) and references cited therein.].
43. Effect of bismuth (III) iodide on the improvement of enantio-selectivity in the catalytic asymmetric hydrogenation was previously shown. See Yukimoto, Y.; Kanai, K.; Inanaga, M. In Abstracts of Papers: The 112th Annual Meeting of the Pharmaceutical Society of Japan, 1992; Vol. 2, p 109.
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