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Volumn 72, Issue 3, 2007, Pages 1020-1023

Highly enantioselective hydrogenation of α-dehydroamino esters and itaconates with triphosphorous bidentate ligands and the unprecedented solvent effect thereof

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMINES; CATALYST SELECTIVITY; HYDROGENATION; PALLADIUM COMPOUNDS; PHOSPHORUS COMPOUNDS; SOLVENTS; X RAY DIFFRACTION ANALYSIS;

EID: 33846895705     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0622429     Document Type: Article
Times cited : (49)

References (31)
  • 12
    • 0034678893 scopus 로고    scopus 로고
    • For other representative phosphine-phosphoramidite ligands in hydrogenation, see: a
    • For other representative phosphine-phosphoramidite ligands in hydrogenation, see: (a) Francio, G.; Faraone, F.; Leitner, W. Angew. Chem., Int. Ed. 2000, 39, 1428.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 1428
    • Francio, G.1    Faraone, F.2    Leitner, W.3
  • 16
    • 33846937470 scopus 로고    scopus 로고
    • So far, we have not been able to obtain a suitable single crystal of Rh/1 for the X-ray diffraction experiment. However, the structure of an isoelectronic Pd(II) complex may provide valuable coordination information as well. See, for example: Bayer, A.; Murszat, P.; Thewalt, U.; Rieger, B. Eur. J. Inorg. Chem. 2002, 2614.
    • So far, we have not been able to obtain a suitable single crystal of Rh/1 for the X-ray diffraction experiment. However, the structure of an isoelectronic Pd(II) complex may provide valuable coordination information as well. See, for example: Bayer, A.; Murszat, P.; Thewalt, U.; Rieger, B. Eur. J. Inorg. Chem. 2002, 2614.
  • 25
    • 14944379368 scopus 로고    scopus 로고
    • Aware of this issue, our group recently developed DuanPhos as both enantiomers compared with the previously reported TangPhos, which exists as only one enantiomer. See
    • Aware of this issue, our group recently developed DuanPhos as both enantiomers compared with the previously reported TangPhos, which exists as only one enantiomer. See: Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646.
    • (2005) Eur. J. Org. Chem , pp. 646
    • Liu, D.1    Zhang, X.2
  • 26
    • 20444466430 scopus 로고    scopus 로고
    • In heterogeneous hydrogenation, reversal of enantioselectivity is under active study. See, for example
    • (a) In heterogeneous hydrogenation, reversal of enantioselectivity is under active study. See, for example: Bonalumi, N.; Vargas, A.; Ferri, D.; Burgi, T.; Mallat, T.; Baiker, A. J. Am. Chem. Soc. 2005, 127, 8467.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 8467
    • Bonalumi, N.1    Vargas, A.2    Ferri, D.3    Burgi, T.4    Mallat, T.5    Baiker, A.6
  • 27
    • 33750921617 scopus 로고    scopus 로고
    • In asymmetric transfer hydrogenation, it was shown very recently that a subtle change in ligand structure can result in a switch of the product's absolute configurations. See: Zaitsev, A. B, Adolfsson, H. Org. Lett. 2006, 8, 5129
    • (b) In asymmetric transfer hydrogenation, it was shown very recently that a subtle change in ligand structure can result in a switch of the product's absolute configurations. See: Zaitsev, A. B.; Adolfsson, H. Org. Lett. 2006, 8, 5129.
  • 29
    • 33846928829 scopus 로고    scopus 로고
    • A Rh complex of an α-glucosidic bisphosphinite ligand gave 73% ee (S) in ethanol but 6% ee (R) in benzene during the hydrogenation of dehydroamino esters. See: Selke, R. J. Prakt. Chem. 1987, 329, 717.
    • (a) A Rh complex of an α-glucosidic bisphosphinite ligand gave 73% ee (S) in ethanol but 6% ee (R) in benzene during the hydrogenation of dehydroamino esters. See: Selke, R. J. Prakt. Chem. 1987, 329, 717.
  • 30
    • 25444510405 scopus 로고    scopus 로고
    • 2 but 26% ee (S) in MeOH during the hydrogenation of an enol acetate. See: Panella, L.; Feringa, B. L.; de Vires, J. G.; Minnaard, A. J. Org. Lett. 2005, 7, 4177.
    • 2 but 26% ee (S) in MeOH during the hydrogenation of an enol acetate. See: Panella, L.; Feringa, B. L.; de Vires, J. G.; Minnaard, A. J. Org. Lett. 2005, 7, 4177.
  • 31
    • 33846920242 scopus 로고    scopus 로고
    • 2·1a, the distance from P(3) to P(2) is 3.906 Å, from P(3) to N(1) is 3.779 Å, and from P(3) to Pd(1) is 5.499 Å.
    • 2·1a, the distance from P(3) to P(2) is 3.906 Å, from P(3) to N(1) is 3.779 Å, and from P(3) to Pd(1) is 5.499 Å.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.