DOI: 10.1016/s0957-4166(00)00315-3. Palladium(0)-catalyzed asymmetric synthesis of 2-vinylmorpholine and 2-vinylpiperazine. Influence of the biscarbonate structure on the enantioselectivity

Palladium(0)-catalyzed asymmetric synthesis of 2-vinylmorpholine and 2-vinylpiperazine. Influence of the biscarbonate structure on the enantioselectivity

10.1016/s0957-4166(00)00315-3

Crossref journal-article

Elsevier BV

Tetrahedron: Asymmetry (78)

Bibliography

Massacret, M., Lakhmiri, R., Lhoste, P., Nguefack, C., Ben Abdelouahab, F. B., Fadel, R., & Sinou, D. (2000). Palladium(0)-catalyzed asymmetric synthesis of 2-vinylmorpholine and 2-vinylpiperazine. Influence of the biscarbonate structure on the enantioselectivity. Tetrahedron: Asymmetry, 11(17), 3561â3568.

Authors 7

Magali Massacret (first)
Rajae Lakhmiri (additional)
Paul Lhoste (additional)
Christelle Nguefack (additional)
Fouad B Ben Abdelouahab (additional)
Rachid Fadel (additional)
Denis Sinou (additional)

References 23 Referenced 31

(a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38–52. (10.1002/anie.198900381)
(b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp. 29–61. (10.1016/B978-0-08-052349-1.00119-0)
10.1002/jhet.5570310305 / J. Heterocycl. Chem. by Grigg (1994)
10.1002/anie.199423791 / Angew. Chem., Int. Ed. Engl. by De Meijere (1994)
{'key': '10.1016/S0957-4166(00)00315-3_BIB4', 'series-title': 'Cyclization Reactions', 'first-page': '255', 'author': 'Thebtaranonth', 'year': '1994'} / Cyclization Reactions by Thebtaranonth (1994)
Tietze, L. F. Chem. Ind. (London) 1995, 453–457.
(a) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975–1015. (10.1016/0040-4020(94)01011-N)
(b) 1996, 52, 9289–9346.
10.1021/cr950020x / Chem. Rev. by Negishi (1996)
10.1021/cr950065y / Chem. Rev. by Ojima (1996)
(a) Massacret, M.; Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1994, 35, 6093–6096. (10.1016/0040-4039(94)88084-0)
(b) Massacret, M.; Lhoste, P.; Lakhmiri, R.; Parella, T.; Sinou, D. Eur. J. Org. Chem. 1999, 2665–2673. (10.1002/(SICI)1099-0690(199910)1999:10<2665::AID-EJOC2665>3.0.CO;2-0)
10.1021/jo00076a052 / J. Org. Chem. by Uozomi (1993)
10.1016/0957-4166(96)00018-3 / Tetrahedron: Asymmetry by Yamazaki (1996)
{'key': '10.1016/S0957-4166(00)00315-3_BIB12', 'first-page': '343', 'volume': '134', 'author': 'Lhoste', 'year': '1997', 'journal-title': 'Bull. Soc. Chim. Fr.'} / Bull. Soc. Chim. Fr. by Lhoste (1997)
10.1016/0957-4166(95)00114-5 / Tetrahedron: Asymmetry by Yamazaki (1995)
Massacret, M.; Lhoste, P.; Sinou, D. Eur. J. Org. Chem. 1999, 129–134. (10.1002/(SICI)1099-0690(199901)1999:1<129::AID-EJOC129>3.0.CO;2-6)
(a) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297–6298. (10.1021/ja960649x)
(b) Pfaltz, A.; Roch, G. Tetrahedron: Asymmetry 1996, 7, 2213–2216. (10.1016/0957-4166(96)00274-1)
(c) Trost, B. M.; Asakawa, N. Synthesis 1999, 1491–1494. (10.1055/s-1999-3649)
10.1021/jo00297a077 / J. Org. Chem. by Tsuda (1990)
10.1021/ja01287a016 / J. Am. Chem. Soc. by Amundsen (1937)
Boothroy, B.; Clark, E. R. J. Chem. Soc. 1953, 1499–1504. (10.1039/jr9530001499)

Dates

Type	When
Created	23 years, 1 month ago (July 25, 2002, 6:38 a.m.)
Deposited	6 years, 4 months ago (May 2, 2019, 2:56 p.m.)
Indexed	3 months, 1 week ago (May 26, 2025, 8:27 p.m.)
Issued	25 years ago (Sept. 1, 2000)
Published	25 years ago (Sept. 1, 2000)
Published Print	25 years ago (Sept. 1, 2000)

Funders 0

None

BibTeX

@article{Massacret_2000, title={Palladium(0)-catalyzed asymmetric synthesis of 2-vinylmorpholine and 2-vinylpiperazine. Influence of the biscarbonate structure on the enantioselectivity}, volume={11}, ISSN={0957-4166}, url={http://dx.doi.org/10.1016/s0957-4166(00)00315-3}, DOI={10.1016/s0957-4166(00)00315-3}, number={17}, journal={Tetrahedron: Asymmetry}, publisher={Elsevier BV}, author={Massacret, Magali and Lakhmiri, Rajae and Lhoste, Paul and Nguefack, Christelle and Ben Abdelouahab, Fouad B and Fadel, Rachid and Sinou, Denis}, year={2000}, month=sep, pages={3561–3568} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        5,
        27
      ]
    ],
    "date-time": "2025-05-27T00:27:38Z",
    "timestamp": 1748305658922
  },
  "reference-count": 23,
  "publisher": "Elsevier BV",
  "issue": "17",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2000,
            9,
            1
          ]
        ],
        "date-time": "2000-09-01T00:00:00Z",
        "timestamp": 967766400000
      },
      "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": [
      [
        2000,
        9
      ]
    ]
  },
  "DOI": "10.1016/s0957-4166(00)00315-3",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2002,
        7,
        25
      ]
    ],
    "date-time": "2002-07-25T10:38:29Z",
    "timestamp": 1027593509000
  },
  "page": "3561-3568",
  "source": "Crossref",
  "is-referenced-by-count": 31,
  "title": "Palladium(0)-catalyzed asymmetric synthesis of 2-vinylmorpholine and 2-vinylpiperazine. Influence of the biscarbonate structure on the enantioselectivity",
  "prefix": "10.1016",
  "volume": "11",
  "author": [
    {
      "given": "Magali",
      "family": "Massacret",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Rajae",
      "family": "Lakhmiri",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Paul",
      "family": "Lhoste",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Christelle",
      "family": "Nguefack",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Fouad B",
      "family": "Ben Abdelouahab",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Rachid",
      "family": "Fadel",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Denis",
      "family": "Sinou",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "78",
  "reference": [
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB1.1",
      "doi-asserted-by": "crossref",
      "unstructured": "(a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38\u201352.",
      "DOI": "10.1002/anie.198900381"
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB1.2",
      "doi-asserted-by": "crossref",
      "unstructured": "(b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp. 29\u201361.",
      "DOI": "10.1016/B978-0-08-052349-1.00119-0"
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB2",
      "doi-asserted-by": "crossref",
      "first-page": "631",
      "DOI": "10.1002/jhet.5570310305",
      "volume": "31",
      "author": "Grigg",
      "year": "1994",
      "journal-title": "J. Heterocycl. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB3",
      "doi-asserted-by": "crossref",
      "first-page": "2379",
      "DOI": "10.1002/anie.199423791",
      "volume": "33",
      "author": "De Meijere",
      "year": "1994",
      "journal-title": "Angew. Chem., Int. Ed. Engl."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB4",
      "series-title": "Cyclization Reactions",
      "first-page": "255",
      "author": "Thebtaranonth",
      "year": "1994"
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB5",
      "unstructured": "Tietze, L. F. Chem. Ind. (London) 1995, 453\u2013457."
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB6.1",
      "doi-asserted-by": "crossref",
      "unstructured": "(a) Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975\u20131015.",
      "DOI": "10.1016/0040-4020(94)01011-N"
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB6.2",
      "unstructured": "(b) 1996, 52, 9289\u20139346."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB7",
      "doi-asserted-by": "crossref",
      "first-page": "365",
      "DOI": "10.1021/cr950020x",
      "volume": "96",
      "author": "Negishi",
      "year": "1996",
      "journal-title": "Chem. Rev."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB8",
      "doi-asserted-by": "crossref",
      "first-page": "635",
      "DOI": "10.1021/cr950065y",
      "volume": "96",
      "author": "Ojima",
      "year": "1996",
      "journal-title": "Chem. Rev."
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB9.1",
      "doi-asserted-by": "crossref",
      "unstructured": "(a) Massacret, M.; Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1994, 35, 6093\u20136096.",
      "DOI": "10.1016/0040-4039(94)88084-0"
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB9.2",
      "doi-asserted-by": "crossref",
      "unstructured": "(b) Massacret, M.; Lhoste, P.; Lakhmiri, R.; Parella, T.; Sinou, D. Eur. J. Org. Chem. 1999, 2665\u20132673.",
      "DOI": "10.1002/(SICI)1099-0690(199910)1999:10<2665::AID-EJOC2665>3.0.CO;2-0"
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB10",
      "doi-asserted-by": "crossref",
      "first-page": "6826",
      "DOI": "10.1021/jo00076a052",
      "volume": "58",
      "author": "Uozomi",
      "year": "1993",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB11",
      "doi-asserted-by": "crossref",
      "first-page": "403",
      "DOI": "10.1016/0957-4166(96)00018-3",
      "volume": "7",
      "author": "Yamazaki",
      "year": "1996",
      "journal-title": "Tetrahedron: Asymmetry"
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB12",
      "first-page": "343",
      "volume": "134",
      "author": "Lhoste",
      "year": "1997",
      "journal-title": "Bull. Soc. Chim. Fr."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB13",
      "doi-asserted-by": "crossref",
      "first-page": "1021",
      "DOI": "10.1016/0957-4166(95)00114-5",
      "volume": "6",
      "author": "Yamazaki",
      "year": "1995",
      "journal-title": "Tetrahedron: Asymmetry"
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB14",
      "doi-asserted-by": "crossref",
      "unstructured": "Massacret, M.; Lhoste, P.; Sinou, D. Eur. J. Org. Chem. 1999, 129\u2013134.",
      "DOI": "10.1002/(SICI)1099-0690(199901)1999:1<129::AID-EJOC129>3.0.CO;2-6"
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB15.1",
      "doi-asserted-by": "crossref",
      "unstructured": "(a) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297\u20136298.",
      "DOI": "10.1021/ja960649x"
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB15.2",
      "doi-asserted-by": "crossref",
      "unstructured": "(b) Pfaltz, A.; Roch, G. Tetrahedron: Asymmetry 1996, 7, 2213\u20132216.",
      "DOI": "10.1016/0957-4166(96)00274-1"
    },
    {
      "key": "#cr-split#-10.1016/S0957-4166(00)00315-3_BIB15.3",
      "doi-asserted-by": "crossref",
      "unstructured": "(c) Trost, B. M.; Asakawa, N. Synthesis 1999, 1491\u20131494.",
      "DOI": "10.1055/s-1999-3649"
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB16",
      "doi-asserted-by": "crossref",
      "first-page": "3388",
      "DOI": "10.1021/jo00297a077",
      "volume": "55",
      "author": "Tsuda",
      "year": "1990",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB17",
      "doi-asserted-by": "crossref",
      "first-page": "1466",
      "DOI": "10.1021/ja01287a016",
      "volume": "59",
      "author": "Amundsen",
      "year": "1937",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "10.1016/S0957-4166(00)00315-3_BIB18",
      "doi-asserted-by": "crossref",
      "unstructured": "Boothroy, B.; Clark, E. R. J. Chem. Soc. 1953, 1499\u20131504.",
      "DOI": "10.1039/jr9530001499"
    }
  ],
  "container-title": "Tetrahedron: Asymmetry",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.elsevier.com/content/article/PII:S0957416600003153?httpAccept=text/xml",
      "content-type": "text/xml",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://api.elsevier.com/content/article/PII:S0957416600003153?httpAccept=text/plain",
      "content-type": "text/plain",
      "content-version": "vor",
      "intended-application": "text-mining"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2019,
        5,
        2
      ]
    ],
    "date-time": "2019-05-02T18:56:33Z",
    "timestamp": 1556823393000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://linkinghub.elsevier.com/retrieve/pii/S0957416600003153"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2000,
        9
      ]
    ]
  },
  "references-count": 23,
  "journal-issue": {
    "issue": "17",
    "published-print": {
      "date-parts": [
        [
          2000,
          9
        ]
      ]
    }
  },
  "alternative-id": [
    "S0957416600003153"
  ],
  "URL": "http://dx.doi.org/10.1016/S0957-4166(00)00315-3",
  "relation": {},
  "ISSN": [
    "0957-4166"
  ],
  "subject": [],
  "container-title-short": "Tetrahedron: Asymmetry",
  "published": {
    "date-parts": [
      [
        2000,
        9
      ]
    ]
  }
}