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Volumn 126, Issue 6, 2004, Pages 1612-1613

The Brønsted Acid-Catalyzed Direct Aza-Darzens Synthesis of N-Alkyl cis-Aziridines

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDIMINE; ALIPHATIC AMINE; AZIRIDINE DERIVATIVE; BRONSTED ACID; HETEROCYCLIC COMPOUND; IMINE; LEWIS ACID; SCHIFF BASE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 1242336837     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0385282     Document Type: Article
Times cited : (127)

References (29)
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    • note
    • For example: solid zinc chloride (Aldrich): $8/mole versus gaseous hydrochloric acid (Matheson): $0.23/mole.
  • 8
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    • Jacobsen. E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin
    • (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen. E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin; 1999; Vol. 2, p 607.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 607
  • 12
    • 0003591704 scopus 로고
    • Pearson, R. G., Ed.; Doweden, Hutchinson. & Ross: Stroudsberg
    • (b) Hard and Soft Acids and Bases; Pearson, R. G., Ed.; Doweden, Hutchinson. & Ross: Stroudsberg, 1973.
    • (1973) Hard and Soft Acids and Bases
  • 20
    • 0002813232 scopus 로고
    • Wiley: New York
    • Pizey, J. S. Synthetic Reagents; Wiley: New York, 1974; Vol. 2, pp 65-142.
    • (1974) Synthetic Reagents , vol.2 , pp. 65-142
    • Pizey, J.S.1
  • 22
    • 0037244819 scopus 로고    scopus 로고
    • For leading references to the use of the more electrophilic α-imino esters in asymmetric synthesis, see: Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 10
    • Taggi, A.E.1    Hafez, A.M.2    Lectka, T.3
  • 23
    • 0037023469 scopus 로고    scopus 로고
    • The failure of ethyl diazoacetate to react directly with imines more electron deficient than 2 has been noted by others: Aggarwal, V. K.; Alonso, E. ; Ferrara, M.; Spey, S. E. J. Org. Chem. 2002, 67, 2335.
    • (2002) J. Org. Chem. , vol.67 , pp. 2335
    • Aggarwal, V.K.1    Alonso, E.2    Ferrara, M.3    Spey, S.E.4
  • 24
    • 85087238472 scopus 로고    scopus 로고
    • note
    • 2CN at -78°C.
  • 25
    • 85087241645 scopus 로고    scopus 로고
    • note
    • 2Et (both olefin isomers) are most common. See ref 2 for additional details.
  • 26
    • 1242324831 scopus 로고    scopus 로고
    • note
    • The depressed yield is due to noticeable decomposition of aziridine 4h during purification.
  • 27
    • 24244445147 scopus 로고    scopus 로고
    • For a special issue of reviews on "Green Chemistry", see: Chem. Rev. 2002, 102.
    • (2002) Chem. Rev. , pp. 102


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.