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Volumn , Issue 9, 2003, Pages 1765-1774

Synthesis of novel 4-(2-oxoethylidene)azetidin-2-ones by a Lewis acid mediated reaction of acyldiazo compounds

Author keywords

Diazo compounds; Lactams; Lewis acids

Indexed keywords

4 (2 OXOETHYLIDENE)AZETIDIN 2 ONE DERIVATIVE; AZETIDINONE DERIVATIVE; AZO COMPOUND; BETA LACTAM; LEWIS ACID; UNCLASSIFIED DRUG;

EID: 0037989827     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200210702     Document Type: Article
Times cited : (33)

References (68)
  • 34
    • 0002709357 scopus 로고
    • S. Mickel, Aldrichimica Acta 1985, 18, 95; T. Nagahara, T. Kametani, Heterocycles 1987, 25, 729. For a comprehensive review, see: A. H. Berks, Tetrahedron 1996, 52, 331, and references cited therein.
    • (1985) Aldrichimica Acta , vol.18 , pp. 95
    • Mickel, S.1
  • 35
    • 0345798442 scopus 로고
    • S. Mickel, Aldrichimica Acta 1985, 18, 95; T. Nagahara, T. Kametani, Heterocycles 1987, 25, 729. For a comprehensive review, see: A. H. Berks, Tetrahedron 1996, 52, 331, and references cited therein.
    • (1987) Heterocycles , vol.25 , pp. 729
    • Nagahara, T.1    Kametani, T.2
  • 36
    • 0030028910 scopus 로고    scopus 로고
    • and references cited therein
    • S. Mickel, Aldrichimica Acta 1985, 18, 95; T. Nagahara, T. Kametani, Heterocycles 1987, 25, 729. For a comprehensive review, see: A. H. Berks, Tetrahedron 1996, 52, 331, and references cited therein.
    • (1996) Tetrahedron , vol.52 , pp. 331
    • Berks, A.H.1
  • 38
    • 0000709206 scopus 로고
    • T. Ye, A. McKervey, Chem. Rev. 1994, 94, 1091; M. P. Doyle, M. A McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, John Wiley and Sons, New York, 1998.
    • (1994) Chem. Rev , vol.94 , pp. 1091
    • Ye, T.1    McKervey, A.2
  • 43
    • 0023605420 scopus 로고
    • Ethyl {(2R,3S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]4-oxoazetidin-2-yl} acetate was obtained in good yields from 1a and ethyl bromoacetate by means of a Reformatsky reaction. See: Y. Ito, S. Terashima, Tetrahedron Lett. 1987, 29, 6625.
    • (1987) Tetrahedron Lett. , vol.29 , pp. 6625
    • Ito, Y.1    Terashima, S.2
  • 55
    • 0038606600 scopus 로고    scopus 로고
    • note
    • One of the referees has suggested that the less-efficient reaction with 3-haloazetidin-2-ones may also result from a Lewis acid mediated halide abstraction leading to a carbenium ion that then decays by an unidentified pathway.
  • 56
    • 0037930341 scopus 로고    scopus 로고
    • note
    • These intermediates must be transient species, because attempts to isolate these diazo intermediates failed.
  • 60
    • 84955394357 scopus 로고    scopus 로고
    • (Ed.: H. Yamamoto), Wiley-VCH, Weinheim
    • Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000.
    • (2000) Lewis Acids in Organic Synthesis


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.