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Volumn 41, Issue 26, 2000, Pages 4999-5003

From serine to functionalized enantiopure tetrahydroisoquinolines

Author keywords

Conjugate addition; Friedel Crafts; Organocuprate

Indexed keywords

SERINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE;

EID: 0034709568     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00765-6     Document Type: Article
Times cited : (38)

References (26)
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    • and references cited therein
    • Rozwadowska, M.D. Heterocycles 1994, 39, 903, and references cited therein; Herbert, R.B. In The Chemistry and Biology of Isoquinoline Alkaloids; Philipson, J. D.; Roberts, M. F.; Zenk, M. H., Eds.; Springer-Verlag: Berlin, 1985; p. 213; Shamma, M. In Isoquinoline Alkaloids, Chemistry and Pharmacology; Academic: New York, 1972.
    • (1994) Heterocycles , vol.39 , pp. 903
    • Rozwadowska, M.D.1
  • 2
    • 0002592667 scopus 로고
    • Philipson, J. D.; Roberts, M. F.; Zenk, M. H., Eds.; Springer-Verlag: Berlin
    • Rozwadowska, M.D. Heterocycles 1994, 39, 903, and references cited therein; Herbert, R.B. In The Chemistry and Biology of Isoquinoline Alkaloids; Philipson, J. D.; Roberts, M. F.; Zenk, M. H., Eds.; Springer-Verlag: Berlin, 1985; p. 213; Shamma, M. In Isoquinoline Alkaloids, Chemistry and Pharmacology; Academic: New York, 1972.
    • (1985) The Chemistry and Biology of Isoquinoline Alkaloids , pp. 213
    • Herbert, R.B.1
  • 3
    • 0003818285 scopus 로고
    • Academic: New York
    • Rozwadowska, M.D. Heterocycles 1994, 39, 903, and references cited therein; Herbert, R.B. In The Chemistry and Biology of Isoquinoline Alkaloids; Philipson, J. D.; Roberts, M. F.; Zenk, M. H., Eds.; Springer-Verlag: Berlin, 1985; p. 213; Shamma, M. In Isoquinoline Alkaloids, Chemistry and Pharmacology; Academic: New York, 1972.
    • (1972) Isoquinoline Alkaloids, Chemistry and Pharmacology
    • Shamma, M.1
  • 7
    • 0032567398 scopus 로고    scopus 로고
    • For leading references, see: Vicario, J.L.; Badía, D.; Domínguez, E.; Carrillo, L. J. Org. Chem. 1999, 64, 4610; Monsees, A.; Laschat, S.; Dix, I. J. Org. Chem. 1998, 63, 10018.
    • (1998) J. Org. Chem. , vol.63 , pp. 10018
    • Monsees, A.1    Laschat, S.2    Dix, I.3
  • 10
    • 8344249465 scopus 로고    scopus 로고
    • For the synthesis of heterocycles from amino acids
    • For the synthesis of heterocycles from amino acids, see: Sardina, F.J.; Rapoport, H. Chem. Rev. 1996, 96, 1825; for early seminal work in asymmetric synthesis, see: Meyers, A.I.; Fuentes, L.M. J. Am. Chem. Soc. 1983, 105, 117.
    • (1996) Chem. Rev. , vol.96 , pp. 1825
    • Sardina, F.J.1    Rapoport, H.2
  • 11
    • 0000945801 scopus 로고
    • for early seminal work in asymmetric synthesis
    • For the synthesis of heterocycles from amino acids, see: Sardina, F.J.; Rapoport, H. Chem. Rev. 1996, 96, 1825; for early seminal work in asymmetric synthesis, see: Meyers, A.I.; Fuentes, L.M. J. Am. Chem. Soc. 1983, 105, 117.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 117
    • Meyers, A.I.1    Fuentes, L.M.2
  • 16
    • 0024841697 scopus 로고
    • For a review on α-amino acid aldehydes, their derivatives, and further transformations
    • For a review on α-amino acid aldehydes, their derivatives, and further transformations, see: Reetz, M.T.; Röhrig, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706; Reetz, M.T. Chem. Rev. 1999, 99, 1121.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 1706
    • Reetz, M.T.1    Röhrig, D.2
  • 17
    • 0000763561 scopus 로고    scopus 로고
    • For a review on α-amino acid aldehydes, their derivatives, and further transformations
    • For a review on α-amino acid aldehydes, their derivatives, and further transformations, see: Reetz, M.T.; Röhrig, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1706; Reetz, M.T. Chem. Rev. 1999, 99, 1121.
    • (1999) Chem. Rev. , vol.99 , pp. 1121
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    • note
    • 4 and concentrated in vacuo to give after flash chromatography (petroleum ether:AcOEt. 3:1 then 1:1) 370 mg (72%) of 6 as a colorless oil.
  • 24
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    • See, for example: Hanessian, S.; Tyler, P. C.; Demailly, G.; Chapleur, Y. J. Am. Chem. Soc. 1981, 103, 6243; Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 1409.
    • (1975) Tetrahedron Lett. , pp. 1409
    • Nakagawa, I.1    Hata, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.