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Volumn 64, Issue 26, 1999, Pages 9596-9604

Novel diethylaluminum chloride promoted reactions of the azetidine ring: Efficient and stereocontrolled entry to functionalized olefins, pyrrolidines, and pyrroles

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALUMINUM DERIVATIVE; AZETIDINE DERIVATIVE; BETA LACTAM ANTIBIOTIC; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE;

EID: 0033601329     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991203c     Document Type: Article
Times cited : (64)

References (60)
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    • Padwa, A., Eds; Elsevier: Oxford, Chapter 1.18
    • For reviews on the synthesis and chemistry of azetidines, see: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Eds; Elsevier: Oxford, 1996; Vol. 1B, Chapter 1.18, pp 507-589.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.1 B , pp. 507-589
    • De Kimpe, N.1
  • 40
    • 0000008267 scopus 로고
    • For some selected examples reporting the bizarre effects caused by the inhibition of NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Dominguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5604
    • Alcaide, B.1    Casarrubios, L.2    Dominguez, G.3    Sierra, M.A.4    Monge, A.5
  • 45
    • 0006371410 scopus 로고
    • (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805.
    • (1987) J. Org. Chem. , vol.52 , pp. 805
    • Slebocka-Tilk, H.1    Brown, R.S.2
  • 47
    • 0343953124 scopus 로고    scopus 로고
    • note
    • β-Lactams 1 were prepared in multigram quantities by standard acid chloride-imine cyclization, and were used as single cis- or trans-diastereomers throughout this work.
  • 51
    • 0001314546 scopus 로고
    • 2-Alkoxy azetidines, putative intermediates in the transforma-tion of β-chloroimines to β-(alkylamino)carbonyl compounds, have been postulated to experience a related N1-C2 bond breakage, in basic alkoxide media. Sulmon, P.; De Kimpe, N.; Schamp, N. Tetrahedron 1989, 45, 2937.
    • (1989) Tetrahedron , vol.45 , pp. 2937
    • Sulmon, P.1    De Kimpe, N.2    Schamp, N.3
  • 52
    • 0000002236 scopus 로고
    • Padwa, A., Ed.; Wiley: New York
    • Because of the importance of substituted, stereoisomerically pure pyrrolidines as building blocks for the synthesis of natural products and pharmaceuticals, their stereocontrolled synthesis remains an intensive research area. See, for example: (a) Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, p 653.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1 , pp. 653
    • Lown, J.W.1
  • 53
    • 0000693487 scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier: New York
    • (b) Pearson, W. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: New York, 1988; Vol. 1, Part A, p 323.
    • (1988) Studies in Natural Products Chemistry , vol.1 , Issue.PART A , pp. 323
    • Pearson, W.H.1
  • 60
    • 0343517211 scopus 로고    scopus 로고
    • note
    • Full spectroscopic and analytical data for compounds not included in the Experimental Section are described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.