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Volumn , Issue 16, 2007, Pages 2541-2544

A simple and efficient catalyst system for the asymmetric transfer hydrogenation of ketones

Author keywords

Asymmetric catalysis; Hydrogen transfer; Ketones; Reductions; Rhodium

Indexed keywords

2 PROPANOL; ACETOPHENONE; AMINO ACID; HYDROXAMIC ACID; KETONE DERIVATIVE; LIGAND; RHODIUM;

EID: 35348962716     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-986653     Document Type: Article
Times cited : (24)

References (48)
  • 2
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    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
    • (b) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 199.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 199
    • Ohkuma, T.1    Noyori, R.2
  • 11
    • 7044252416 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: New York
    • (k) Ohkuma, T.; Noyori, R. Comprehensive Asymmetric Catalalysis, Suppl. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 2004, 43.
    • (2004) Comprehensive Asymmetric Catalalysis , Issue.SUPPL. 1 , pp. 43
    • Ohkuma, T.1    Noyori, R.2
  • 15
    • 3543040636 scopus 로고    scopus 로고
    • For recent selected examples, see: a
    • For recent selected examples, see: (a) Brandt, P.; Roth, P.; Andersson, P. G. J. Org. Chem. 2004, 69, 4885.
    • (2004) J. Org. Chem , vol.69 , pp. 4885
    • Brandt, P.1    Roth, P.2    Andersson, P.G.3
  • 28
    • 0001704256 scopus 로고    scopus 로고
    • For other examples of amino acid based ligands in the transfer hydrogenation of ketones, see: a
    • For other examples of amino acid based ligands in the transfer hydrogenation of ketones, see: (a) Ohta, T.; Nakahara, S.; Shigemura, Y.; Hattori, K.; Furokawa, I. Chem. Lett. 1998, 491.
    • (1998) Chem. Lett , pp. 491
    • Ohta, T.1    Nakahara, S.2    Shigemura, Y.3    Hattori, K.4    Furokawa, I.5
  • 31
    • 35348945003 scopus 로고    scopus 로고
    • Kathó, ; Carmona, D.; Viguri, F.; Remacha, C. D.; Kovács, J.; Joó, F.; Oro, L. A. J. Organomet. Chem. 2000, 593-594, 209.
    • (d) Kathó, ; Carmona, D.; Viguri, F.; Remacha, C. D.; Kovács, J.; Joó, F.; Oro, L. A. J. Organomet. Chem. 2000, 593-594, 209.
  • 38
    • 22744455748 scopus 로고    scopus 로고
    • Highly efficient vanadium catalysts containing ligands based on hydroxamic acids were recently employed in the asymmetric epoxidation of allylic alcohols, see: (a) Zhang, W, Basak, A, Kosugi, Y, Hoshino, Y, Yamamoto, H. Angew. Chem. Int. Ed. 2005, 44, 4389. For selected earlier reports, see
    • Highly efficient vanadium catalysts containing ligands based on hydroxamic acids were recently employed in the asymmetric epoxidation of allylic alcohols, see: (a) Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem. Int. Ed. 2005, 44, 4389. For selected earlier reports, see:
  • 45
    • 35349012350 scopus 로고    scopus 로고
    • General Procedure for the Preparation of Hydroxamic Acid Ligands 1a-d To a solution of 2,4,6-trichloro-1,3,5-triazine (0.1 mmol) in anhyd CH2Cl2 (8 mL) cooled to 0°C, the following components were added in the order they are written: Bocprotected amino acid (3 mmol, NMM (6 mmol, DMAP (0.3 mmol, and NH2OH·HCl (3 mmol, The reaction mixture was stirred at r.t. for 14 h and thereafter filtered through a plug of silica, using EtOAc as eluent. The residue obtained after evaporation of the filtrate was chromatographed on silica (EtOAc-pentane, 10:1, followed by recrystallization from acetone-pentane to give the hydroxamic acids. Compound 1a: yield 41, 1H NMR (400 MHz, acetone-d6, 25°C, δ, 10.09 (s, 1 H, 8.22 (br s, 1 H, 6.06 (s, 1 H, 4.08 (q, J, 7.11 Hz, 1 H, 1.40 (s, 9 H, 1.29 (d, J, 7.11 Hz, 3 H, 13C NMR 100 MHz, acetone-d6, 25°C
    • 6, 25°C): δ = 167.3, 154.7, 138.9, 128.3, 127.6, 127.0, 78.6, 55.7, 27.5.
  • 46
    • 37049076654 scopus 로고    scopus 로고
    • For the original report on the importance of external base in transition-metal-catalyzed transfer-hydrogenation reactions, see: Chowdhury, R. L, Bäckvall, J.-E. J. Chem. Soc, Chem. Commun. 1991, 1063
    • For the original report on the importance of external base in transition-metal-catalyzed transfer-hydrogenation reactions, see: Chowdhury, R. L.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1991, 1063.
  • 47
    • 35348988368 scopus 로고    scopus 로고
    • 2] (0.0025 mmol), ligand (0.0055 mmol), and LiCl (0.05 mmol) were dried under vacuum in a dry Schlenk tube for 15 min. Ketone (1 mmol), i-PrOH (4.5 mL), and a 0.01 M solution of i-PrONa in i-PrOH (0.5 mL, 5 mol%) were added under nitrogen. The reaction mixture was stirred at ambient temperature. Aliquots were taken after the reaction times indicated in Tables 1 and 2 and were then passed through a pad of silica with EtOAc as the eluent. The resulting solutions were analyzed by GLC (CP Chirasil DEXCB).
    • 2] (0.0025 mmol), ligand (0.0055 mmol), and LiCl (0.05 mmol) were dried under vacuum in a dry Schlenk tube for 15 min. Ketone (1 mmol), i-PrOH (4.5 mL), and a 0.01 M solution of i-PrONa in i-PrOH (0.5 mL, 5 mol%) were added under nitrogen. The reaction mixture was stirred at ambient temperature. Aliquots were taken after the reaction times indicated in Tables 1 and 2 and were then passed through a pad of silica with EtOAc as the eluent. The resulting solutions were analyzed by GLC (CP Chirasil DEXCB).
  • 48
    • 35348951207 scopus 로고    scopus 로고
    • Turnover frequencies determined after 30 min reaction time
    • Turnover frequencies determined after 30 min reaction time.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.