DOI: 10.1016/s0957-4166(00)00500-0. Investigation into the enantioselective protonation of enolate Schiff bases with (R)-pantolactone

Investigation into the enantioselective protonation of enolate Schiff bases with (R)-pantolactone

10.1016/s0957-4166(00)00500-0

Crossref journal-article

Elsevier BV

Tetrahedron: Asymmetry (78)

Bibliography

CalmÃ¨s, M., Glot, C., & Martinez, J. (2001). Investigation into the enantioselective protonation of enolate Schiff bases with (R)-pantolactone. Tetrahedron: Asymmetry, 12(1), 49â52.

Authors 3

Monique Calmès (first)
Christèle Glot (additional)
Jean Martinez (additional)

References 36 Referenced 5

10.1002/anie.199625661 / Angew. Chem., Int. Ed. Engl. by Fehr (1996)
{'key': '10.1016/S0957-4166(00)00500-0_BIB3', 'first-page': '125', 'volume': '282c', 'author': 'Duhamel', 'year': '1976', 'journal-title': 'C. R. Acad. Sci.'} / C. R. Acad. Sci. by Duhamel (1976)
10.1021/ja00491a050 / J. Am. Chem. Soc. by Duhamel (1978)
{'key': '10.1016/S0957-4166(00)00500-0_BIB5', 'first-page': '75', 'author': 'Duhamel', 'year': '1982', 'journal-title': 'Bull. Soc. Chim. Fr. II'} / Bull. Soc. Chim. Fr. II by Duhamel (1982)
10.1016/S0040-4039(00)85111-4 / Tetrahedron Lett. by Duhamel (1986)
10.1021/jo990897m / J. Org. Chem. by Vedejs (1999)
10.1016/0040-4039(95)02170-1 / Tetrahedron Lett. by Calmès (1996)
10.1016/S0957-4166(97)00143-2 / Tetrahedron: Asymmetry by Calmès (1997)
10.1016/S0957-4166(98)00313-9 / Tetrahedron: Asymmetry by Calmès (1998)
10.1016/S0040-4039(00)92293-7 / Tetrahedron Lett. by Matsumoto (1991)
10.1002/anie.198712831 / Angew. Chem., Int. Ed. Engl. by Gerlach (1987)
10.1002/cber.19941271022 / Chem. Ber. by Gerlach (1994)
10.1016/S0957-4166(00)82229-6 / Tetrahedron: Asymmetry by Cavelier (1993)
Thermodynamic conditions: Enolization by addition of the ester 1 to a pre-cooled solution of the base (no self-condensation is observed)
Kinetic conditions: enolization by addition of the base to a pre-cooled solution of the ester 1, see Ref. 7.
10.1021/jo01016a001 / J. Org. Chem. by House (1965)
10.1021/ja00426a033 / J. Am. Chem. Soc. by Ireland (1976)
10.1021/ja00294a010 / J. Am. Chem. Soc. by Moreland (1985)
10.1021/jo00002a030 / J. Org. Chem. by Ireland (1991)
10.1021/jo00129a038 / J. Org. Chem. by Alvarrez-Ibarra (1995)
10.1021/jo00088a048 / J. Org. Chem. by Solladié-Cavallo (1994)
10.1021/ja00108a005 / J. Am. Chem. Soc. by Vedejs (1995)
10.1002/hlca.19850680530 / Helv. Chim. Acta by Laube (1985)
10.1002/hlca.19850680603 / Helv. Chim. Acta by Aebi (1985)
10.1002/anie.198816241 / Angew. Chem., Int. Ed. Engl. by Seebach (1988)
10.1016/S0040-4039(00)99281-5 / Tetrahedron Lett. by O'Donnel (1989)
The enantiomeric composition was determined from the NMR spectra (C6D6) for the crude product in the presence of the chiral shift reagent Eu(hfc)3 by integration of the signals of the diastereoisomeric complexes and/or by HPLC (Nucleosil C18) after deprotection of the amine function and reaction with Marfey's reagent (Marfey, P. Carlsberg Res. Commun. 1984, 49, 591–596). (10.1007/BF02908688)
10.1021/jo981294y / J. Org. Chem. by Asensio (1998)
10.1016/S0022-328X(00)80594-X / J. Organomet. Chem. by Kimura (1971)
Hünig, S. Stereoselective Synthesis; Houben-Weyl 1996, 7, 3851–3911.
10.1016/S0957-4166(00)86011-5 / Tetrahedron: Asymmetry by Yasukata (1993)
10.1055/s-1998-1594 / Synlett by Yanagisawa (1998)
10.1016/S0040-4039(98)00469-9 / Tetrahedron Lett. by Asensio (1998)
10.1016/S0040-4020(98)00482-7 / Tetrahedron by Yanagisawa (1998)
10.1002/hlca.19820650141 / Helv. Chim. Acta by Mukhopadhyay (1982)
10.1016/S0957-4166(97)84908-7 / Tetrahedron: Asymmetry by Muzart (1997)

Dates

Type	When
Created	23 years, 1 month ago (July 25, 2002, 11:56 a.m.)
Deposited	5 years, 7 months ago (Jan. 15, 2020, 10:29 a.m.)
Indexed	3 weeks, 3 days ago (Aug. 6, 2025, 9:14 a.m.)
Issued	24 years, 6 months ago (Feb. 1, 2001)
Published	24 years, 6 months ago (Feb. 1, 2001)
Published Print	24 years, 6 months ago (Feb. 1, 2001)

Funders 0

None

BibTeX

@article{Calm_s_2001, title={Investigation into the enantioselective protonation of enolate Schiff bases with (R)-pantolactone}, volume={12}, ISSN={0957-4166}, url={http://dx.doi.org/10.1016/s0957-4166(00)00500-0}, DOI={10.1016/s0957-4166(00)00500-0}, number={1}, journal={Tetrahedron: Asymmetry}, publisher={Elsevier BV}, author={Calmès, Monique and Glot, Christèle and Martinez, Jean}, year={2001}, month=feb, pages={49–52} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        6
      ]
    ],
    "date-time": "2025-08-06T13:14:15Z",
    "timestamp": 1754486055707
  },
  "reference-count": 36,
  "publisher": "Elsevier BV",
  "issue": "1",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2001,
            2,
            1
          ]
        ],
        "date-time": "2001-02-01T00:00:00Z",
        "timestamp": 980985600000
      },
      "content-version": "tdm",
      "delay-in-days": 0,
      "URL": "https://www.elsevier.com/tdm/userlicense/1.0/"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2001,
        2
      ]
    ]
  },
  "DOI": "10.1016/s0957-4166(00)00500-0",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2002,
        7,
        25
      ]
    ],
    "date-time": "2002-07-25T15:56:29Z",
    "timestamp": 1027612589000
  },
  "page": "49-52",
  "source": "Crossref",
  "is-referenced-by-count": 5,
  "title": "Investigation into the enantioselective protonation of enolate Schiff bases with (R)-pantolactone",
  "prefix": "10.1016",
  "volume": "12",
  "author": [
    {
      "given": "Monique",
      "family": "Calm\u00e8s",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Christ\u00e8le",
      "family": "Glot",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Jean",
      "family": "Martinez",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "78",
  "reference": [
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB1",
      "doi-asserted-by": "crossref",
      "first-page": "2566",
      "DOI": "10.1002/anie.199625661",
      "volume": "35",
      "author": "Fehr",
      "year": "1996",
      "journal-title": "Angew. Chem., Int. Ed. Engl."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB3",
      "first-page": "125",
      "volume": "282c",
      "author": "Duhamel",
      "year": "1976",
      "journal-title": "C. R. Acad. Sci."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB4",
      "doi-asserted-by": "crossref",
      "first-page": "7415",
      "DOI": "10.1021/ja00491a050",
      "volume": "100",
      "author": "Duhamel",
      "year": "1978",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB5",
      "first-page": "75",
      "author": "Duhamel",
      "year": "1982",
      "journal-title": "Bull. Soc. Chim. Fr. II"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB6",
      "doi-asserted-by": "crossref",
      "first-page": "4975",
      "DOI": "10.1016/S0040-4039(00)85111-4",
      "volume": "27",
      "author": "Duhamel",
      "year": "1986",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB7",
      "doi-asserted-by": "crossref",
      "first-page": "7863",
      "DOI": "10.1021/jo990897m",
      "volume": "64",
      "author": "Vedejs",
      "year": "1999",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB9",
      "doi-asserted-by": "crossref",
      "first-page": "379",
      "DOI": "10.1016/0040-4039(95)02170-1",
      "volume": "37",
      "author": "Calm\u00e8s",
      "year": "1996",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB10",
      "doi-asserted-by": "crossref",
      "first-page": "1641",
      "DOI": "10.1016/S0957-4166(97)00143-2",
      "volume": "8",
      "author": "Calm\u00e8s",
      "year": "1997",
      "journal-title": "Tetrahedron: Asymmetry"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB11",
      "doi-asserted-by": "crossref",
      "first-page": "2845",
      "DOI": "10.1016/S0957-4166(98)00313-9",
      "volume": "9",
      "author": "Calm\u00e8s",
      "year": "1998",
      "journal-title": "Tetrahedron: Asymmetry"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB12",
      "doi-asserted-by": "crossref",
      "first-page": "4729",
      "DOI": "10.1016/S0040-4039(00)92293-7",
      "volume": "32",
      "author": "Matsumoto",
      "year": "1991",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB14",
      "doi-asserted-by": "crossref",
      "first-page": "1283",
      "DOI": "10.1002/anie.198712831",
      "volume": "26",
      "author": "Gerlach",
      "year": "1987",
      "journal-title": "Angew. Chem., Int. Ed. Engl."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB15",
      "doi-asserted-by": "crossref",
      "first-page": "1981",
      "DOI": "10.1002/cber.19941271022",
      "volume": "127",
      "author": "Gerlach",
      "year": "1994",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB16",
      "doi-asserted-by": "crossref",
      "first-page": "2501",
      "DOI": "10.1016/S0957-4166(00)82229-6",
      "volume": "4",
      "author": "Cavelier",
      "year": "1993",
      "journal-title": "Tetrahedron: Asymmetry"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB18",
      "unstructured": "Thermodynamic conditions: Enolization by addition of the ester 1 to a pre-cooled solution of the base (no self-condensation is observed)"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB19",
      "unstructured": "Kinetic conditions: enolization by addition of the base to a pre-cooled solution of the ester 1, see Ref. 7."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB21",
      "doi-asserted-by": "crossref",
      "first-page": "1341",
      "DOI": "10.1021/jo01016a001",
      "volume": "30",
      "author": "House",
      "year": "1965",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB22",
      "doi-asserted-by": "crossref",
      "first-page": "2868",
      "DOI": "10.1021/ja00426a033",
      "volume": "98",
      "author": "Ireland",
      "year": "1976",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB23",
      "doi-asserted-by": "crossref",
      "first-page": "2264",
      "DOI": "10.1021/ja00294a010",
      "volume": "107",
      "author": "Moreland",
      "year": "1985",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB24",
      "doi-asserted-by": "crossref",
      "first-page": "650",
      "DOI": "10.1021/jo00002a030",
      "volume": "56",
      "author": "Ireland",
      "year": "1991",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB25",
      "doi-asserted-by": "crossref",
      "first-page": "7934",
      "DOI": "10.1021/jo00129a038",
      "volume": "60",
      "author": "Alvarrez-Ibarra",
      "year": "1995",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB27",
      "doi-asserted-by": "crossref",
      "first-page": "2585",
      "DOI": "10.1021/jo00088a048",
      "volume": "59",
      "author": "Solladi\u00e9-Cavallo",
      "year": "1994",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB28",
      "doi-asserted-by": "crossref",
      "first-page": "891",
      "DOI": "10.1021/ja00108a005",
      "volume": "117",
      "author": "Vedejs",
      "year": "1995",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB30",
      "doi-asserted-by": "crossref",
      "first-page": "1373",
      "DOI": "10.1002/hlca.19850680530",
      "volume": "68",
      "author": "Laube",
      "year": "1985",
      "journal-title": "Helv. Chim. Acta"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB31",
      "doi-asserted-by": "crossref",
      "first-page": "1507",
      "DOI": "10.1002/hlca.19850680603",
      "volume": "68",
      "author": "Aebi",
      "year": "1985",
      "journal-title": "Helv. Chim. Acta"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB32",
      "doi-asserted-by": "crossref",
      "first-page": "1624",
      "DOI": "10.1002/anie.198816241",
      "volume": "27",
      "author": "Seebach",
      "year": "1988",
      "journal-title": "Angew. Chem., Int. Ed. Engl."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB33",
      "doi-asserted-by": "crossref",
      "first-page": "3909",
      "DOI": "10.1016/S0040-4039(00)99281-5",
      "volume": "30",
      "author": "O'Donnel",
      "year": "1989",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB34",
      "doi-asserted-by": "crossref",
      "unstructured": "The enantiomeric composition was determined from the NMR spectra (C6D6) for the crude product in the presence of the chiral shift reagent Eu(hfc)3 by integration of the signals of the diastereoisomeric complexes and/or by HPLC (Nucleosil C18) after deprotection of the amine function and reaction with Marfey's reagent (Marfey, P. Carlsberg Res. Commun. 1984, 49, 591\u2013596).",
      "DOI": "10.1007/BF02908688"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB35",
      "doi-asserted-by": "crossref",
      "first-page": "9342",
      "DOI": "10.1021/jo981294y",
      "volume": "63",
      "author": "Asensio",
      "year": "1998",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB37",
      "doi-asserted-by": "crossref",
      "first-page": "57",
      "DOI": "10.1016/S0022-328X(00)80594-X",
      "volume": "26",
      "author": "Kimura",
      "year": "1971",
      "journal-title": "J. Organomet. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB38",
      "unstructured": "H\u00fcnig, S. Stereoselective Synthesis; Houben-Weyl 1996, 7, 3851\u20133911."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB40",
      "doi-asserted-by": "crossref",
      "first-page": "35",
      "DOI": "10.1016/S0957-4166(00)86011-5",
      "volume": "4",
      "author": "Yasukata",
      "year": "1993",
      "journal-title": "Tetrahedron: Asymmetry"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB41",
      "doi-asserted-by": "crossref",
      "first-page": "174",
      "DOI": "10.1055/s-1998-1594",
      "author": "Yanagisawa",
      "year": "1998",
      "journal-title": "Synlett"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB42",
      "doi-asserted-by": "crossref",
      "first-page": "3277",
      "DOI": "10.1016/S0040-4039(98)00469-9",
      "volume": "39",
      "author": "Asensio",
      "year": "1998",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB43",
      "doi-asserted-by": "crossref",
      "first-page": "10253",
      "DOI": "10.1016/S0040-4020(98)00482-7",
      "volume": "54",
      "author": "Yanagisawa",
      "year": "1998",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB44",
      "doi-asserted-by": "crossref",
      "first-page": "385",
      "DOI": "10.1002/hlca.19820650141",
      "volume": "65",
      "author": "Mukhopadhyay",
      "year": "1982",
      "journal-title": "Helv. Chim. Acta"
    },
    {
      "key": "10.1016/S0957-4166(00)00500-0_BIB45",
      "doi-asserted-by": "crossref",
      "first-page": "381",
      "DOI": "10.1016/S0957-4166(97)84908-7",
      "volume": "8",
      "author": "Muzart",
      "year": "1997",
      "journal-title": "Tetrahedron: Asymmetry"
    }
  ],
  "container-title": "Tetrahedron: Asymmetry",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.elsevier.com/content/article/PII:S0957416600005000?httpAccept=text/xml",
      "content-type": "text/xml",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://api.elsevier.com/content/article/PII:S0957416600005000?httpAccept=text/plain",
      "content-type": "text/plain",
      "content-version": "vor",
      "intended-application": "text-mining"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2020,
        1,
        15
      ]
    ],
    "date-time": "2020-01-15T15:29:11Z",
    "timestamp": 1579102151000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://linkinghub.elsevier.com/retrieve/pii/S0957416600005000"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2001,
        2
      ]
    ]
  },
  "references-count": 36,
  "journal-issue": {
    "issue": "1",
    "published-print": {
      "date-parts": [
        [
          2001,
          2
        ]
      ]
    }
  },
  "alternative-id": [
    "S0957416600005000"
  ],
  "URL": "http://dx.doi.org/10.1016/S0957-4166(00)00500-0",
  "relation": {},
  "ISSN": [
    "0957-4166"
  ],
  "subject": [],
  "container-title-short": "Tetrahedron: Asymmetry",
  "published": {
    "date-parts": [
      [
        2001,
        2
      ]
    ]
  }
}