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Volumn 6, Issue 15, 2004, Pages 2571-2574

Stereoselective iodocyclization of 3-acylamino-2-methylene alkanoates: Synthesis of analogues of N-benzoyl-syn-phenylisoserine

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOIC ACID; CARBENE; ISOSERINE; N BENZOYLPHENYLISOSERINE; UNCLASSIFIED DRUG;

EID: 4043184283     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049146j     Document Type: Article
Times cited : (56)

References (44)
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    • Cardillo, G.1    Tomasini, C.2
  • 2
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    • Wiley-VCH: New York
    • For reviews, see: (a) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128. (b) Enantioselective Synthesis of β-Amino Acids: Juaristi, E., Ed.; Wiley-VCH: New York, 1996. (c) Seebach, D.; Mattews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015-2022. (d) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
    • (1996) Enantioselective Synthesis of β-Amino Acids
    • Juaristi, E.1
  • 3
    • 14844312173 scopus 로고    scopus 로고
    • For reviews, see: (a) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128. (b) Enantioselective Synthesis of β-Amino Acids: Juaristi, E., Ed.; Wiley-VCH: New York, 1996. (c) Seebach, D.; Mattews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015-2022. (d) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 2015-2022
    • Seebach, D.1    Mattews, J.L.2
  • 4
    • 0542421525 scopus 로고    scopus 로고
    • For reviews, see: (a) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117-128. (b) Enantioselective Synthesis of β-Amino Acids: Juaristi, E., Ed.; Wiley-VCH: New York, 1996. (c) Seebach, D.; Mattews, J. L. J. Chem. Soc., Chem. Commun. 1997, 2015-2022. (d) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
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    • Gellman, S.H.1
  • 6
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    • Paclitaxel (Taxol) Chemistry and Structure-Activity Relationships
    • Farina, V., Ed.; Elsevier: Amsterdam
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    • (1995) The Chemistry and Pharmacology of Taxol and Its Derivatives , pp. 165-253
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  • 7
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    • The Medicinal Chemistry of Taxol
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  • 27
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    • Amination Reactions Promoted by Electrophiles
    • Helmchen, G., Hofmann, R. W., Mulzer, J., Schauman, E., Eds., Thieme: Stuttgart
    • (b) Orena, M. Amination Reactions Promoted by Electrophiles. In Houhen-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G., Hofmann, R. W., Mulzer, J., Schauman, E., Eds., Thieme: Stuttgart, 1995; Vol. E 21e, pp 5291-5355.
    • (1995) Houhen-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis , vol.E 21E , pp. 5291-5355
    • Orena, M.1
  • 30
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    • and references therein
    • All reactions were performed starting from racemic amides, but β-amino acids can be obtained in the enantiomerically pure form by kinetic resolution of their phenylacetamides with penicillin G acylase. So, by using enantiomerically pure starting materials, our approach leads to enantiomerically pure compounds. See: Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. J. Org. Chem. 1998, 63, 2351-2353, and references therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 2351-2353
    • Cardillo, G.1    Gentilucci, L.2    Tolomelli, A.3    Tomasini, C.4
  • 31
    • 0000630028 scopus 로고
    • A single example of iodocyclization of Baylis-Hillman adducts was found in the literature: Drewes, S. E.; Njamela, O. L.; Roos, G. H. P. Chem. Ber. 1990, 123, 2455-2456.
    • (1990) Chem. Ber. , vol.123 , pp. 2455-2456
    • Drewes, S.E.1    Njamela, O.L.2    Roos, G.H.P.3
  • 35
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    • note
    • -1. Duplicate conformations and conformations with an energy excess of 5 kcal/mol above the global minimum were discarded.
  • 42
    • 4043103372 scopus 로고    scopus 로고
    • note
    • 3SnH was employed, tin derivatives unseparable from 3a were produced in the reduction reaction.
  • 43
    • 4043128891 scopus 로고    scopus 로고
    • note
    • Compound 8d was employed, in place of 8a, since cleavage of the ester function of 8a was observed under nucleophilic substitution reaction conditions.
  • 44
    • 0033538666 scopus 로고    scopus 로고
    • Hydroxyamination of Baylis-Hillman adducts was already reported: Pringle, W.; Sharpless, K. B. Tetrahedron Lett. 1999, 40, 5151-5154.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5151-5154
    • Pringle, W.1    Sharpless, K.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.