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Volumn 74, Issue 11, 2009, Pages 4177-4187

AmIno Acid Homologation by the Blaise Reaction: A new entry into nitrogen heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC HYDROLYSIS; AMINO NITRILES; ASPARTIC ACIDS; CHEMICAL EQUATIONS; FUNCTIONALIZED; NITROGEN HETEROCYCLES; REDUCTION CONDITIONS; SUBSEQUENT REDUCTION;

EID: 66249093821     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900324d     Document Type: Article
Times cited : (49)

References (83)
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    • Erasmus student from Åarhus University, Denmark
    • Erasmus student from Åarhus University, Denmark.
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    • For recent applications of the cyanoborohydride reduction of enamino esters, see
    • For recent applications of the cyanoborohydride reduction of enamino esters, see: (a) Alladoum, J.; Dechoux, L. Tetrahedron Lett. 2005, 46, 8203.
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    • Alladoum, J.1    Dechoux, L.2
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    • All compounds described from now on were synthesized in both racemic and enantiomerically pure form. The enantiomeric purity of each intermediate was checked by HPLC on chiral column
    • All compounds described from now on were synthesized in both racemic and enantiomerically pure form. The enantiomeric purity of each intermediate was checked by HPLC on chiral column.
  • 45
    • 66249133619 scopus 로고    scopus 로고
    • Control experiments showed that cyclization occurred before potassium carbonate workup. Adding sodium hydride before this workup did not improve the yields
    • Control experiments showed that cyclization occurred before potassium carbonate workup. Adding sodium hydride before this workup did not improve the yields.
  • 49
    • 66249131238 scopus 로고    scopus 로고
    • In contrast, Blaise reaction with the L-glutamic acid derived amino nitrile led to a mixture of products arizing from both possible cyclizations. Unpublished results
    • In contrast, Blaise reaction with the L-glutamic acid derived amino nitrile led to a mixture of products arizing from both possible cyclizations. Zulauf, A.; Alezra, V.; Kouklovsky, C. Unpublished results.
    • Zulauf, A.1    Alezra, V.2    Kouklovsky, C.3
  • 53
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    • The enantiomeric purity of each of stereoisomers of 38 was determined by HPLC after trifluoroacetylation (see Supporting Information)
    • The enantiomeric purity of each of stereoisomers of 38 was determined by HPLC after trifluoroacetylation (see Supporting Information).
  • 54
    • 0034741042 scopus 로고    scopus 로고
    • For a discussion about the stereoselectivity of the reduction of related ketones, see: and references therein
    • For a discussion about the stereoselectivity of the reduction of related ketones, see: Liang, X.; Andersch, J.; Bols, M. J. Chem Soc., Perkin Trans. 1 2001, 2136, and references therein.
    • (2001) J. Chem Soc., Perkin Trans. 1 , pp. 2136
    • Liang, X.1    Andersch, J.2    Bols, M.3
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    • Rhodium-catalyzed hydrogenation of (Z)-enamino esters
    • Rhodium-catalyzed hydrogenation of (Z)-enamino esters: (a) Yan, Y.; Zhang, X. Tetrahedron Lett. 2006, 47, 1567.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 1567
    • Yan, Y.1    Zhang, X.2
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    • Rhodium-catalyzed hydrogenation of (E)-enamino esters
    • Rhodium-catalyzed hydrogenation of (E)-enamino esters: (a) Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3509.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3509
    • Tang, W.1    Wang, W.2    Chi, Y.3    Zhang, X.4
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    • Ruthenium-catalyzed hydrogenation of enamino esters
    • Ruthenium-catalyzed hydrogenation of enamino esters: Wu, J.; Chen, X.; Guo, R.; Yueng, C.-H.; Chan, A. S. C. J. Org. Chem. 2003, 68, 2490.
    • (2003) J. Org. Chem. , vol.68 , pp. 2490
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    • The enantiomeric purity of lactam 42 was determined after conversion into its Fmoc carbamate (see Supporting Information)
    • The enantiomeric purity of lactam 42 was determined after conversion into its Fmoc carbamate (see Supporting Information).
  • 73
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    • Reviews: Georg Thieme Verlag: Stuttgart
    • Reviews: (a) Venturello, P.; Barbero, M. In Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2005; 8b, p 881.
    • (2005) Science of Synthesis , vol.8 B , pp. 881
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    • For a table of chemical shifts, see Supporting Information
    • For a table of chemical shifts, see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.