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Volumn 72, Issue 10, 2007, Pages 3859-3862

Asymmetric route to pyridines bearing a highly functionalized 2-alkyl substituent by aziridine ring-opening reactions

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; DERIVATIVES; HYDRATES; NUCLEOPHILES; PYRIDINE; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 34248572962     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070364a     Document Type: Article
Times cited : (23)

References (31)
  • 3
    • 33748605775 scopus 로고
    • Asymmetric synthesis of aziridines and their applications as chiral ligands or auxiliaries: (a) Tanner, D
    • Asymmetric synthesis of aziridines and their applications as chiral ligands or auxiliaries: (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
    • (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 599-619
  • 13
    • 1542375289 scopus 로고    scopus 로고
    • (d) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 15
    • 33746497862 scopus 로고    scopus 로고
    • For recent reports on ring-opening of 1-(1-phenylethyl)-2-acylaziridines by acid chlorides and anhydrides, see: a
    • For recent reports on ring-opening of 1-(1-phenylethyl)-2-acylaziridines by acid chlorides and anhydrides, see: (a) Kim, Y.; Ha, H.-J.; Yun, H.; Lee, B. K.; Lee, W. K. Tetrahedron 2006, 62, 8844-8849.
    • (2006) Tetrahedron , vol.62 , pp. 8844-8849
    • Kim, Y.1    Ha, H.-J.2    Yun, H.3    Lee, B.K.4    Lee, W.K.5
  • 20
    • 0037037889 scopus 로고    scopus 로고
    • Ring-opening of N-tosyl aziridines by water in the presence of cerium ammonium nitrate has been reported: Chandrasekhar, S.; Narsihmulu, Ch.; Shameem Sultana, S. Tetrahedron Lett. 2002, 43, 7361-7363.
    • Ring-opening of N-tosyl aziridines by water in the presence of cerium ammonium nitrate has been reported: Chandrasekhar, S.; Narsihmulu, Ch.; Shameem Sultana, S. Tetrahedron Lett. 2002, 43, 7361-7363.
  • 21
    • 0000677635 scopus 로고    scopus 로고
    • N-Tosyl aziridines were cleaved by sodium azide in the same conditions: Sabitha, G.; Babu, R. S.; Rajkumar, M.; Yadav, J. S. Org. Lett. 2002, 4, 343-345.
    • N-Tosyl aziridines were cleaved by sodium azide in the same conditions: Sabitha, G.; Babu, R. S.; Rajkumar, M.; Yadav, J. S. Org. Lett. 2002, 4, 343-345.
  • 23
    • 27844510033 scopus 로고    scopus 로고
    • 3 cleaved N-tosyl and N-alkyl aziridines in polar aprotic solvents: (a) Wu, J.; Sun, X.; Xia, H.-G. Eur. J. Org. Chem. 2005, 4769-4772.
    • 3 cleaved N-tosyl and N-alkyl aziridines in polar aprotic solvents: (a) Wu, J.; Sun, X.; Xia, H.-G. Eur. J. Org. Chem. 2005, 4769-4772.
  • 28
    • 0036139236 scopus 로고    scopus 로고
    • N-Activated aziridines were cleaved by primary amines in the presence of lithium perchlorate: (a) Yadav, J. S.; Reddy, B. V. S.; Jyothirmai, B.; Murty, M. S. R. Synlett 2002, 53-56.
    • N-Activated aziridines were cleaved by primary amines in the presence of lithium perchlorate: (a) Yadav, J. S.; Reddy, B. V. S.; Jyothirmai, B.; Murty, M. S. R. Synlett 2002, 53-56.
  • 30
    • 27744475785 scopus 로고    scopus 로고
    • Similarly, 1,2-disubstituted aziridines in the presence of boron trifluoride underwent selective opening by attack of thiols at the substituted aziridine carbon: Concellon, J. M.; Bernad, P. L.; Suárez, J. R. J. Org. Chem. 2005, 70, 9411-9416.
    • Similarly, 1,2-disubstituted aziridines in the presence of boron trifluoride underwent selective opening by attack of thiols at the substituted aziridine carbon: Concellon, J. M.; Bernad, P. L.; Suárez, J. R. J. Org. Chem. 2005, 70, 9411-9416.
  • 31
    • 0033551722 scopus 로고    scopus 로고
    • 1,2-Dialkylaziridines were cleaved by thiols in dichloromethane by attack at the unsubstituted aziridine carbon: Bae, J. H.; Shin, S.-H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041-10046.
    • 1,2-Dialkylaziridines were cleaved by thiols in dichloromethane by attack at the unsubstituted aziridine carbon: Bae, J. H.; Shin, S.-H.; Park, C. S.; Lee, W. K. Tetrahedron 1999, 55, 10041-10046.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.