메뉴 건너뛰기




Volumn 74, Issue 3, 2009, Pages 1411-1414

Ru-TsDPEN with formic acid/hunig's base for asymmetric transfer hydrogenation, a practical synthesis of optically enriched N-propyl pantolactam

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC TRANSFER HYDROGENATIONS; ASYMMETRIC TRANSFERS; CHEMICAL YIELDS; CHIRAL PURITIES; N PROPYLS;

EID: 64549133435     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802380j     Document Type: Article
Times cited : (51)

References (63)
  • 11
    • 64549160166 scopus 로고    scopus 로고
    • Borane-based reductants and hydrogen gas are considered as highly toxic or hazardous chemicals and require additional safety considerations when used on large scale
    • Borane-based reductants and hydrogen gas are considered as highly toxic or hazardous chemicals and require additional safety considerations when used on large scale.
  • 12
    • 12344271397 scopus 로고    scopus 로고
    • 2nd ed, Beller, M, Bolm, C, Eds, Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany
    • (a) Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals, 2nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2004; Vol. 2, pp 145-162.
    • (2004) Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals , vol.2 , pp. 145-162
  • 13
    • 17844369291 scopus 로고    scopus 로고
    • Murahashi, S.-I, Ed, Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany
    • (b) Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2004; pp 3-41.
    • (2004) Ruthenium in Organic Synthesis , pp. 3-41
  • 18
    • 54549105366 scopus 로고    scopus 로고
    • For some recent reviews on asymmetric transfer hydrogenation, see:a
    • For some recent reviews on asymmetric transfer hydrogenation, see:(a) Wang, C.; Wu, X.; Xiao, J. Chem. Asian, J. 2008, 3, 1750.
    • (2008) Chem. Asian, J , vol.3 , pp. 1750
    • Wang, C.1    Wu, X.2    Xiao, J.3
  • 23
    • 84891013428 scopus 로고    scopus 로고
    • Wills, M. In Modern Reductive Methods; Andersson, P. G., Munslow, I. J., Eds.; Wiley-VCH: Weinheim, Germany, 2008; pp 271-296.
    • (d) Wills, M. In Modern Reductive Methods; Andersson, P. G., Munslow, I. J., Eds.; Wiley-VCH: Weinheim, Germany, 2008; pp 271-296.
  • 24
    • 84869272013 scopus 로고    scopus 로고
    • 2/ DMF, which eliminated epimerization; however, the conversion was low at room temperature. Heating the reaction to 40 °C increased the yield to 52%, but the ratio of R/S dropped to 85/15 from 95/5.
    • 2/ DMF, which eliminated epimerization; however, the conversion was low at room temperature. Heating the reaction to 40 °C increased the yield to 52%, but the ratio of R/S dropped to 85/15 from 95/5.
  • 25
    • 0037697887 scopus 로고    scopus 로고
    • Enantioselective hydrogenation of ketopantolactone was achieved with a Pt catalyst modified by cinchonidine at high pressure (69-70 atm, giving the R-pantolactone 3 with 92% ee. See: (a) Schurch, M, Kunzle, N, Mallat, T, Baiker, A. J. Catal. 1998, 176, 569
    • Enantioselective hydrogenation of ketopantolactone was achieved with a Pt catalyst modified by cinchonidine at high pressure (69-70 atm), giving the R-pantolactone 3 with 92% ee. See: (a) Schurch, M.; Kunzle, N.; Mallat, T.; Baiker, A. J. Catal. 1998, 176, 569.
  • 27
    • 0034736377 scopus 로고    scopus 로고
    • For some examples, see:(a) Koike, T.; M.; Murata, K.; Ikariya, T. Org. Lett. 2000, 2, 3833.
    • For some examples, see:(a) Koike, T.; M.; Murata, K.; Ikariya, T. Org. Lett. 2000, 2, 3833.
  • 34
    • 64549104782 scopus 로고    scopus 로고
    • Configurations of 9 and 12 were confirmed and assigned based on the configuration of final compound 6
    • manuscript in preparation
    • Configurations of 9 and 12 were confirmed and assigned based on the configuration of final compound 6 (manuscript in preparation).
  • 39
    • 64549153525 scopus 로고    scopus 로고
    • Adding an aprotic polar solvent, such as DMF and NMP, is effective in accelerating the reaction rate during the transfer hydrogenation. See ref 7
    • (a) Adding an aprotic polar solvent, such as DMF and NMP, is effective in accelerating the reaction rate during the transfer hydrogenation. See ref 7.
  • 40
    • 27744449807 scopus 로고    scopus 로고
    • Asymmetric transfer hydrogenation in aqueous media containing micelles and vesicles, see
    • (b) Asymmetric transfer hydrogenation in aqueous media containing micelles and vesicles, see: Wang, F.; Liu, H.; Cun, L.; Zhu, J.; Deng, J.; Jiang, Y. J. Org. Chem. 2005, 70, 9424.
    • (2005) J. Org. Chem , vol.70 , pp. 9424
    • Wang, F.1    Liu, H.2    Cun, L.3    Zhu, J.4    Deng, J.5    Jiang, Y.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.