DOI: 10.1002/anie.199707411. Asymmetric Dihydroxylation with MeO‐Polyethyleneglycol‐Bound Ligands

Asymmetric Dihydroxylation with MeO‐Polyethyleneglycol‐Bound Ligands

10.1002/anie.199707411

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Bibliography

Bolm, C., & Gerlach, A. (1997). Asymmetric Dihydroxylation with MeOâPolyethyleneglycolâBound Ligands. Angewandte Chemie International Edition in English, 36(7), 741â743. Portico.

Authors 2

Carsten Bolm (first)
Arne Gerlach (additional)

References 38 Referenced 68

10.1021/cr00032a009
10.1021/ja00214a053
10.1002/ange.19961080408
10.1002/anie.199604481
10.1021/jo00118a005
10.1021/jo00036a003
10.1021/ja00149a003
10.1016/S0040-4039(00)89009-7
10.1016/S0040-4039(00)93459-2
10.1016/S0040-4039(00)78272-4
10.1016/0957-4166(95)00358-V
10.1016/S0040-4020(01)89433-3
10.1002/chir.530070805
(g)B. B.Lohray E.Nandanan V.Bhushan Tetrahedron: Asymmetry1996 7 2805 and references therein. (10.1016/0957-4166(96)00367-9)
10.1016/0957-4166(96)00054-7
10.1021/ja9608095
(b) see alsoS.Borman Chem. Eng. News1996 August 26 p. 36.
10.1002/ange.19750871304
{'key': 'e_1_2_1_6_5', 'first-page': '493', 'volume': '14', 'year': '1975', 'journal-title': 'Angew. Chem. Int. Ed. Engl.'} / Angew. Chem. Int. Ed. Engl. (1975)
{'key': 'e_1_2_1_6_6', 'first-page': '212', 'volume': '6', 'author': 'Bayer E.', 'year': '1976', 'journal-title': 'Chemtech'} / Chemtech by Bayer E. (1976)
10.1021/jo00049a010
10.1007/978-1-4899-0703-5
{'key': 'e_1_2_1_7_3', 'first-page': '249', 'volume': '9', 'author': 'Delgado C.', 'year': '1992', 'journal-title': 'Crit. Rev. Ther. Drug Carrier Syst.'} / Crit. Rev. Ther. Drug Carrier Syst. by Delgado C. (1992)
10.1016/0169-409X(91)90037-D
10.1016/0169-409X(93)90005-O
10.1073/pnas.92.14.6419
10.1021/ja9535470
10.1002/ange.19951071004
10.1002/anie.199510591
A MeOPEG‐bound (DHQD)2‐PHAL ligand that apparently gives higher enantioselectivities is mentioned in a footnote in ref. [6a] but not specified in more detail.
DHQ = dihydroquinine; DHQD = dihydroquinidine.
10.1021/jo00067a002
MeOPEG was purchased from Fluka (Mr= 5000; number of hydroxy groups OHN = 0.2 mass equiv per gram).
Aryl dibromide8was prepared from pyrazine‐2 3‐dicarboxylic acid in analogy to the corresponding nonhalogenated compound (ref. [3b]).
Theeevalues with N‐methylmorpholine oxide (NMO) are comparably lower: stilbene 99%ee styrene 81%ee 1‐methylstyrene 78%ee.
Sixfold sequential use of3in the AD of styrene resulted in the following enantioselectivities: 98 98 98 98 97 96%ee. The slight decrease in theeevalue can be explained by loss of alkaloid due to minor ester hydrolysis under the basic reaction conditions {[K3Fe(CN)6]/K2CO3}. Other MeOPEG attachments are currently under investigation.
For experimental details see procedure in ref. [12].
Column material: Daicel Chiralcel. Entry 1: bis‐MTPA‐ester (OD) 2: diol (OB); 3: bisbenzoate (OD); 4: bis‐p‐methoxybenzoate (OD) 5:tert‐butyl‐diphenylsilyl monoether (OD).

Dates

Type	When
Created	21 years, 7 months ago (Jan. 16, 2004, 9:08 a.m.)
Deposited	1 year, 10 months ago (Oct. 11, 2023, 7:41 a.m.)
Indexed	1 year, 7 months ago (Jan. 7, 2024, 5:16 a.m.)
Issued	28 years, 4 months ago (April 18, 1997)
Published	28 years, 4 months ago (April 18, 1997)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	28 years, 4 months ago (April 18, 1997)

Funders 0

None

BibTeX

@article{Bolm_1997, title={Asymmetric Dihydroxylation with MeO‐Polyethyleneglycol‐Bound Ligands}, volume={36}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199707411}, DOI={10.1002/anie.199707411}, number={7}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Bolm, Carsten and Gerlach, Arne}, year={1997}, month=apr, pages={741–743} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        1,
        7
      ]
    ],
    "date-time": "2024-01-07T10:16:42Z",
    "timestamp": 1704622602872
  },
  "reference-count": 38,
  "publisher": "Wiley",
  "issue": "7",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            12,
            22
          ]
        ],
        "date-time": "2003-12-22T00:00:00Z",
        "timestamp": 1072051200000
      },
      "content-version": "vor",
      "delay-in-days": 2439,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1997,
        4,
        18
      ]
    ]
  },
  "DOI": "10.1002/anie.199707411",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2004,
        1,
        16
      ]
    ],
    "date-time": "2004-01-16T14:08:21Z",
    "timestamp": 1074262101000
  },
  "page": "741-743",
  "source": "Crossref",
  "is-referenced-by-count": 68,
  "title": "Asymmetric Dihydroxylation with MeO\u2010Polyethyleneglycol\u2010Bound Ligands",
  "prefix": "10.1002",
  "volume": "36",
  "author": [
    {
      "given": "Carsten",
      "family": "Bolm",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Arne",
      "family": "Gerlach",
      "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/cr00032a009"
    },
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00214a053"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19961080408"
    },
    {
      "key": "e_1_2_1_3_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.199604481"
    },
    {
      "key": "e_1_2_1_3_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00118a005"
    },
    {
      "key": "e_1_2_1_3_5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00036a003"
    },
    {
      "key": "e_1_2_1_3_6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00149a003"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)89009-7"
    },
    {
      "key": "e_1_2_1_4_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)93459-2"
    },
    {
      "key": "e_1_2_1_4_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)78272-4"
    },
    {
      "key": "e_1_2_1_4_5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0957-4166(95)00358-V"
    },
    {
      "key": "e_1_2_1_4_6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(01)89433-3"
    },
    {
      "key": "e_1_2_1_4_7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/chir.530070805"
    },
    {
      "key": "e_1_2_1_4_8",
      "doi-asserted-by": "crossref",
      "unstructured": "(g)B. B.Lohray E.Nandanan V.Bhushan Tetrahedron: Asymmetry1996 7 2805 and references therein.",
      "DOI": "10.1016/0957-4166(96)00367-9"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0957-4166(96)00054-7"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja9608095"
    },
    {
      "key": "e_1_2_1_6_3",
      "unstructured": "(b) see alsoS.Borman Chem. Eng. News1996 August 26 p. 36."
    },
    {
      "key": "e_1_2_1_6_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19750871304"
    },
    {
      "key": "e_1_2_1_6_5",
      "first-page": "493",
      "volume": "14",
      "year": "1975",
      "journal-title": "Angew. Chem. Int. Ed. Engl."
    },
    {
      "key": "e_1_2_1_6_6",
      "first-page": "212",
      "volume": "6",
      "author": "Bayer E.",
      "year": "1976",
      "journal-title": "Chemtech"
    },
    {
      "key": "e_1_2_1_6_7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00049a010"
    },
    {
      "key": "e_1_2_1_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/978-1-4899-0703-5"
    },
    {
      "key": "e_1_2_1_7_3",
      "first-page": "249",
      "volume": "9",
      "author": "Delgado C.",
      "year": "1992",
      "journal-title": "Crit. Rev. Ther. Drug Carrier Syst."
    },
    {
      "key": "e_1_2_1_7_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0169-409X(91)90037-D"
    },
    {
      "key": "e_1_2_1_7_5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0169-409X(93)90005-O"
    },
    {
      "key": "e_1_2_1_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1073/pnas.92.14.6419"
    },
    {
      "key": "e_1_2_1_8_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja9535470"
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19951071004"
    },
    {
      "key": "e_1_2_1_9_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.199510591"
    },
    {
      "key": "e_1_2_1_10_2",
      "unstructured": "A MeO\uf8ffPEG\u2010bound (DHQD)2\u2010PHAL ligand that apparently gives higher enantioselectivities is mentioned in a footnote in ref. [6a] but not specified in more detail."
    },
    {
      "key": "e_1_2_1_11_2",
      "unstructured": "DHQ = dihydroquinine; DHQD = dihydroquinidine."
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00067a002"
    },
    {
      "key": "e_1_2_1_13_2",
      "unstructured": "MeO\uf8ffPEG was purchased from Fluka (Mr= 5000; number of hydroxy groups OHN = 0.2 mass equiv per gram)."
    },
    {
      "key": "e_1_2_1_14_2",
      "unstructured": "Aryl dibromide8was prepared from pyrazine\u20102 3\u2010dicarboxylic acid in analogy to the corresponding nonhalogenated compound (ref. [3b])."
    },
    {
      "key": "e_1_2_1_15_2",
      "unstructured": "Theeevalues with N\u2010methylmorpholine oxide (NMO) are comparably lower: stilbene 99%ee styrene 81%ee 1\u2010methylstyrene 78%ee."
    },
    {
      "key": "e_1_2_1_16_2",
      "unstructured": "Sixfold sequential use of3in the AD of styrene resulted in the following enantioselectivities: 98 98 98 98 97 96%ee. The slight decrease in theeevalue can be explained by loss of alkaloid due to minor ester hydrolysis under the basic reaction conditions {[K3Fe(CN)6]/K2CO3}. Other MeO\uf8ffPEG attachments are currently under investigation."
    },
    {
      "key": "e_1_2_1_17_2",
      "unstructured": "For experimental details see procedure in ref. [12]."
    },
    {
      "key": "e_1_2_1_18_2",
      "unstructured": "Column material: Daicel Chiralcel. Entry 1: bis\u2010MTPA\u2010ester (OD) 2: diol (OB); 3: bisbenzoate (OD); 4: bis\u2010p\u2010methoxybenzoate (OD) 5:tert\u2010butyl\u2010diphenylsilyl monoether (OD)."
    }
  ],
  "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.199707411",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.199707411",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        11
      ]
    ],
    "date-time": "2023-10-11T11:41:01Z",
    "timestamp": 1697024461000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.199707411"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1997,
        4,
        18
      ]
    ]
  },
  "references-count": 38,
  "journal-issue": {
    "issue": "7",
    "published-print": {
      "date-parts": [
        [
          1997,
          4,
          18
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.199707411"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.199707411",
  "relation": {},
  "ISSN": [
    "0570-0833"
  ],
  "subject": [],
  "container-title-short": "Angew. Chem. Int. Ed. Engl.",
  "published": {
    "date-parts": [
      [
        1997,
        4,
        18
      ]
    ]
  }
}