DOI: 10.1002/anie.199702851. The Catalyst Precursor, Catalyst, and Intermediate in the Ru<sup>II</sup>‐Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones

The Catalyst Precursor, Catalyst, and Intermediate in the RuII‐Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones

10.1002/anie.199702851

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Bibliography

Haack, K., Hashiguchi, S., Fujii, A., Ikariya, T., & Noyori, R. (1997). The Catalyst Precursor, Catalyst, and Intermediate in the RuIIâPromoted Asymmetric Hydrogen Transfer between Alcohols and Ketones. Angewandte Chemie International Edition in English, 36(3), 285â288. Portico.

Authors 5

Karl‐Josef Haack (first)
Shohei Hashiguchi (additional)
Akio Fujii (additional)
Takao Ikariya (additional)
Ryoji Noyori (additional)

References 28 Referenced 946

10.1021/ja00133a037
(b)J.Takehara S.Hashiguchi A.Fujii S.Inoue T.Ikariya R.Noyori Chem. Commun.1996 233–234; (10.1039/cc9960000233)
10.1021/om950833b
(d)R.Noyori S.Hashiguchi Acc. Chem. Res.1997 30 in press. (10.1021/ar9502341)
10.1002/ange.19971090334
10.1002/anie.199702881
10.1021/ja954126l
10.1021/ja960364k
{'key': 'e_1_2_1_4_2', 'volume-title': 'Asymmetric Synthesis', 'author': 'Halpern J.', 'year': '1985'} / Asymmetric Synthesis by Halpern J. (1985)
(a) Crystal structure analysis of1· 1 H2O: C31H37ClN2O3RuS Mr= 654.23 orange crystal (0.1 × 0.1 × 0.2 mm) orthorhombic space groupP212121(no. 19) a= 14.743(5) b= 24.525(9) c= 8.649(9) Å V= 3127(3) Å3 Z= 4 ρcalcd= 1.39 g cm−3 μ(MoKα) = 6.86 m−1T= 263 K. 3165 Reflections were independent and unique and 2278 withI> 3.00σ(I) (2θmax= 50°) were used for the structure solution. All hydrogen atoms were calculated from ideal geometries fixed and included in the calculation of the structural factor.R= 0.050 Rw= 0.060 w= (σ2(F) + 0.0025F2)−1. Crystal structure analysis of2: C31H34N2O2RuS Mr= 599.75 deep purple crystal (0.1 × 0.1 × 0.1 mm) orthorhombic space groupP212121(no. 19) a= 13.899(5) b= 19.084(4) c= 10.672(3) Å V= 2830(1) Å3 Z= 4 ρcalcd= 1.41 g cm−3 μ(MoKα) = 6.58 cm−1 T= 243 K. 3651 Reflections were independent and unique and 2310 withI> 3.00σ (I) (2θmax= 55°) were used for the structure solution. The hydrogen atom at N1 could be localized and was refined isotropically and the remaining hydrogen atoms were calculated from ideal geometries fixed and included in the calculation of the structure factor.R= 0.036 Rw= 0.033 w= (σ2(F) + 0.0025F2)−1. Crystal structure analysis of3· 2H2O: C31H40‐N2O4RuS Mr= 637.77 yellow crystal (0.1 × 0.1 × 0.1 × mm) orthorhombic space groupP212121(no. 19) a= 15.075(2) b= 18.821(2) c= 11.717(2) Å V= 3324.1(8) Å3 Z= 4 ρcalcd= 1.28 g cm−3 μ(MoKα) = 5.68 cm−1 T= 243 K. 4282 Reflections were independent and unique and 2162 withI> 3.00σ(I) (2θmax= 55°) were used for the structure solution. The hydrogen atoms at N1 and at Ru could be localized and were refined isotropically and the remaining hydrogen atoms were calculated from ideal geometries fixed and included in the calculation of the structural factor.R= 0.050 Rw= 0.067 w= (σ2(F) + 0.0025F2)−1. Rigaku AFC7R diffractometer (graphite monochromator MoKα). The structures were solved with PATTY and DIRDIF94 [5b]. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementry publication no. CCDC‐179‐149. Copies of the data can be obtained free of charge on application to The Director CCDC 12 Union Road Cambridge CB2 1EZ UK (fax: Int. code + (1223)336‐033; e‐mail: deposit@chemcrys.cam.ac.uk) on quoting the full journal citation;
{'key': 'e_1_2_1_5_3', 'volume-title': 'The DIRDIF Program System, Technical Report of the Crystallographic Laboratory', 'author': 'Beurskens P. T.', 'year': '1994'} / The DIRDIF Program System, Technical Report of the Crystallographic Laboratory by Beurskens P. T. (1994)
10.1016/S0022-328X(00)80382-4
10.1021/ja00855a063
10.1021/ja00243a039
10.1016/0010-8545(89)80001-3
10.1021/om00048a025
{'key': 'e_1_2_1_8_2', 'first-page': '1', 'volume': '2', 'author': 'Tobe M. L.', 'year': '1983', 'journal-title': 'Adv. Inorg. Bioinorg. Mech.'} / Adv. Inorg. Bioinorg. Mech. by Tobe M. L. (1983)
10.1021/ja00033a060
10.1021/om00052a037
10.1021/om00001a023
A.Anillo C.Barrio S.Garci'a‐Granda R.Obeso‐Rosete J. Chem. Soc. Dalton Trans.1993 1125–1130. (10.1039/DT9930001125)
10.1016/S0277-5387(00)83602-5
A. K.Burrell A. J.Steedman J. Chem. Soc. Chem. Commun.1995 2109–2110. (10.1039/C39950002109)
{'key': 'e_1_2_1_12_2', 'first-page': '25', 'volume': '18', 'author': 'Caulton K. G.', 'year': '1994', 'journal-title': 'New J. Chem.'} / New J. Chem. by Caulton K. G. (1994)
10.1021/ja953094z
10.1021/ja01030a031
10.1002/9780470132524.ch16
T.Oda R.Irie T.Katsuki H.Okawa Synlett1992 641–643. (10.1055/s-1992-21440)

Dates

Type	When
Created	21 years, 7 months ago (Dec. 31, 2003, 4:31 a.m.)
Deposited	1 year, 10 months ago (Oct. 27, 2023, 4:28 p.m.)
Indexed	11 minutes ago (Aug. 27, 2025, 10:58 p.m.)
Issued	28 years, 6 months ago (Feb. 14, 1997)
Published	28 years, 6 months ago (Feb. 14, 1997)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	28 years, 6 months ago (Feb. 14, 1997)

Funders 0

None

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        28
      ]
    ],
    "date-time": "2025-08-28T02:58:06Z",
    "timestamp": 1756349886821
  },
  "reference-count": 28,
  "publisher": "Wiley",
  "issue": "3",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            12,
            22
          ]
        ],
        "date-time": "2003-12-22T00:00:00Z",
        "timestamp": 1072051200000
      },
      "content-version": "vor",
      "delay-in-days": 2502,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1997,
        2,
        14
      ]
    ]
  },
  "DOI": "10.1002/anie.199702851",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2003,
        12,
        31
      ]
    ],
    "date-time": "2003-12-31T09:31:37Z",
    "timestamp": 1072863097000
  },
  "page": "285-288",
  "source": "Crossref",
  "is-referenced-by-count": 946,
  "title": "The Catalyst Precursor, Catalyst, and Intermediate in the Ru<sup>II</sup>\u2010Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones",
  "prefix": "10.1002",
  "volume": "36",
  "author": [
    {
      "given": "Karl\u2010Josef",
      "family": "Haack",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Shohei",
      "family": "Hashiguchi",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Akio",
      "family": "Fujii",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Takao",
      "family": "Ikariya",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Ryoji",
      "family": "Noyori",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2003,
        12,
        22
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_1_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00133a037"
    },
    {
      "key": "e_1_2_1_1_3",
      "doi-asserted-by": "crossref",
      "unstructured": "(b)J.Takehara S.Hashiguchi A.Fujii S.Inoue T.Ikariya R.Noyori Chem. Commun.1996 233\u2013234;",
      "DOI": "10.1039/cc9960000233"
    },
    {
      "key": "e_1_2_1_1_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/om950833b"
    },
    {
      "key": "e_1_2_1_1_5",
      "doi-asserted-by": "crossref",
      "unstructured": "(d)R.Noyori S.Hashiguchi Acc. Chem. Res.1997 30 in press.",
      "DOI": "10.1021/ar9502341"
    },
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19971090334"
    },
    {
      "key": "e_1_2_1_2_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.199702881"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja954126l"
    },
    {
      "key": "e_1_2_1_3_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja960364k"
    },
    {
      "key": "e_1_2_1_4_2",
      "volume-title": "Asymmetric Synthesis",
      "author": "Halpern J.",
      "year": "1985"
    },
    {
      "key": "e_1_2_1_5_2",
      "unstructured": "(a) Crystal structure analysis of1\u00b7 1 H2O: C31H37ClN2O3RuS Mr= 654.23 orange crystal (0.1 \u00d7 0.1 \u00d7 0.2 mm) orthorhombic space groupP212121(no. 19) a= 14.743(5) b= 24.525(9) c= 8.649(9) \u00c5 V= 3127(3) \u00c53 Z= 4 \u03c1calcd= 1.39 g cm\u22123 \u03bc(MoK\u03b1) = 6.86 m\u22121T= 263 K. 3165 Reflections were independent and unique and 2278 withI> 3.00\u03c3(I) (2\u03b8max= 50\u00b0) were used for the structure solution. All hydrogen atoms were calculated from ideal geometries fixed and included in the calculation of the structural factor.R= 0.050 Rw= 0.060 w= (\u03c32(F) + 0.0025F2)\u22121. Crystal structure analysis of2: C31H34N2O2RuS Mr= 599.75 deep purple crystal (0.1 \u00d7 0.1 \u00d7 0.1 mm) orthorhombic space groupP212121(no. 19) a= 13.899(5) b= 19.084(4) c= 10.672(3) \u00c5 V= 2830(1) \u00c53 Z= 4 \u03c1calcd= 1.41 g cm\u22123 \u03bc(MoK\u03b1) = 6.58 cm\u22121 T= 243 K. 3651 Reflections were independent and unique and 2310 withI> 3.00\u03c3 (I) (2\u03b8max= 55\u00b0) were used for the structure solution. The hydrogen atom at N1 could be localized and was refined isotropically and the remaining hydrogen atoms were calculated from ideal geometries fixed and included in the calculation of the structure factor.R= 0.036 Rw= 0.033 w= (\u03c32(F) + 0.0025F2)\u22121. Crystal structure analysis of3\u00b7 2H2O: C31H40\u2010N2O4RuS Mr= 637.77 yellow crystal (0.1 \u00d7 0.1 \u00d7 0.1 \u00d7 mm) orthorhombic space groupP212121(no. 19) a= 15.075(2) b= 18.821(2) c= 11.717(2) \u00c5 V= 3324.1(8) \u00c53 Z= 4 \u03c1calcd= 1.28 g cm\u22123 \u03bc(MoK\u03b1) = 5.68 cm\u22121 T= 243 K. 4282 Reflections were independent and unique and 2162 withI> 3.00\u03c3(I) (2\u03b8max= 55\u00b0) were used for the structure solution. The hydrogen atoms at N1 and at Ru could be localized and were refined isotropically and the remaining hydrogen atoms were calculated from ideal geometries fixed and included in the calculation of the structural factor.R= 0.050 Rw= 0.067 w= (\u03c32(F) + 0.0025F2)\u22121. Rigaku AFC7R diffractometer (graphite monochromator MoK\u03b1). The structures were solved with PATTY and DIRDIF94 [5b]. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementry publication no. CCDC\u2010179\u2010149. Copies of the data can be obtained free of charge on application to The Director CCDC 12 Union Road Cambridge CB2 1EZ UK (fax: Int. code + (1223)336\u2010033; e\u2010mail: deposit@chemcrys.cam.ac.uk) on quoting the full journal citation;"
    },
    {
      "key": "e_1_2_1_5_3",
      "volume-title": "The DIRDIF Program System, Technical Report of the Crystallographic Laboratory",
      "author": "Beurskens P. T.",
      "year": "1994"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0022-328X(00)80382-4"
    },
    {
      "key": "e_1_2_1_6_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00855a063"
    },
    {
      "key": "e_1_2_1_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00243a039"
    },
    {
      "key": "e_1_2_1_7_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0010-8545(89)80001-3"
    },
    {
      "key": "e_1_2_1_7_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/om00048a025"
    },
    {
      "key": "e_1_2_1_8_2",
      "first-page": "1",
      "volume": "2",
      "author": "Tobe M. L.",
      "year": "1983",
      "journal-title": "Adv. Inorg. Bioinorg. Mech."
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00033a060"
    },
    {
      "key": "e_1_2_1_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/om00052a037"
    },
    {
      "key": "e_1_2_1_10_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/om00001a023"
    },
    {
      "key": "e_1_2_1_10_4",
      "doi-asserted-by": "crossref",
      "unstructured": "A.Anillo C.Barrio S.Garci'a\u2010Granda R.Obeso\u2010Rosete J. Chem. Soc. Dalton Trans.1993 1125\u20131130.",
      "DOI": "10.1039/DT9930001125"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0277-5387(00)83602-5"
    },
    {
      "key": "e_1_2_1_11_3",
      "doi-asserted-by": "crossref",
      "unstructured": "A. K.Burrell A. J.Steedman J. Chem. Soc. Chem. Commun.1995 2109\u20132110.",
      "DOI": "10.1039/C39950002109"
    },
    {
      "key": "e_1_2_1_12_2",
      "first-page": "25",
      "volume": "18",
      "author": "Caulton K. G.",
      "year": "1994",
      "journal-title": "New J. Chem."
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja953094z"
    },
    {
      "key": "e_1_2_1_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01030a031"
    },
    {
      "key": "e_1_2_1_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/9780470132524.ch16"
    },
    {
      "key": "e_1_2_1_16_2",
      "doi-asserted-by": "crossref",
      "unstructured": "T.Oda R.Irie T.Katsuki H.Okawa Synlett1992 641\u2013643.",
      "DOI": "10.1055/s-1992-21440"
    }
  ],
  "container-title": "Angewandte Chemie International Edition in English",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.199702851",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.199702851",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        27
      ]
    ],
    "date-time": "2023-10-27T20:28:53Z",
    "timestamp": 1698438533000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.199702851"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1997,
        2,
        14
      ]
    ]
  },
  "references-count": 28,
  "journal-issue": {
    "issue": "3",
    "published-print": {
      "date-parts": [
        [
          1997,
          2,
          14
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.199702851"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.199702851",
  "relation": {},
  "ISSN": [
    "0570-0833"
  ],
  "subject": [],
  "container-title-short": "Angew. Chem. Int. Ed. Engl.",
  "published": {
    "date-parts": [
      [
        1997,
        2,
        14
      ]
    ]
  }
}