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Volumn 12, Issue 10, 2010, Pages 2290-2293

Carbon-carbon bond formation and pyrrole synthesis via the [3,3] sigmatropic rearrangement of O-vinyl oxime ethers

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ETHER DERIVATIVE; OXIME; PYRROLE DERIVATIVE;

EID: 77952364808     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100659q     Document Type: Article
Times cited : (61)

References (68)
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    • Trost, B. M. and Fleming, I., Eds.; Pergamon: Oxford, UK
    • Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I., Eds.; Pergamon: Oxford, UK, 1991,: Vol. 5, p 827.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 827
    • Wipf, P.1
  • 7
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    • For reviews of the Trofimov reaction see
    • For reviews of the Trofimov reaction see
  • 12
    • 77952324643 scopus 로고    scopus 로고
    • For classic syntheses of pyrroles and reviews of the preparation of pyrroles, see
    • For classic syntheses of pyrroles and reviews of the preparation of pyrroles, see
  • 19
    • 77952348310 scopus 로고    scopus 로고
    • For recent examples of pyrrole syntheses, see
    • For recent examples of pyrrole syntheses, see
  • 26
    • 77952357224 scopus 로고    scopus 로고
    • For examples of the Trofimov reaction with acetylene, see
    • For examples of the Trofimov reaction with acetylene, see
  • 32
    • 77952411538 scopus 로고    scopus 로고
    • For examples of regioisomeric mixtures of products obtained from the use of terminal alkynes in the Trofimov reaction see
    • For examples of regioisomeric mixtures of products obtained from the use of terminal alkynes in the Trofimov reaction see
  • 35
    • 77952325683 scopus 로고    scopus 로고
    • For examples of the biological activity and medicinal application of pyrroles, see
    • For examples of the biological activity and medicinal application of pyrroles, see
  • 42
    • 77952371086 scopus 로고
    • Atorvastin (Lipitor): US4681893
    • Atorvastin (Lipitor): Roth, B. D. US4681893, 1987.
    • (1987)
    • Roth, B.D.1
  • 44
    • 77952365853 scopus 로고    scopus 로고
    • For examples of pyrrole structures in material applications see
    • For examples of pyrrole structures in material applications see
  • 47
    • 77952329464 scopus 로고    scopus 로고
    • For related syntheses of allyl vinyl ethers which undergo subsequent Claisen rearrangements, see
    • For related syntheses of allyl vinyl ethers which undergo subsequent Claisen rearrangements, see
  • 52
    • 77952388225 scopus 로고    scopus 로고
    • For examples of allylic ether isomerizations see
    • For examples of allylic ether isomerizations see
  • 56
    • 77952348309 scopus 로고    scopus 로고
    • See the Supporting Information for full characterization of the O - n -propyl oxime reduction product
    • See the Supporting Information for full characterization of the O-n -propyl oxime reduction product.
  • 59
    • 77952393665 scopus 로고    scopus 로고
    • note
    • O -allyl oxime 1m was synthesized by a substitution reaction between the corresponding oxime and allyl bromide.
  • 60
    • 77952389703 scopus 로고    scopus 로고
    • note
    • 1H nOe experiments. The minor Z-O -allyl oxime isomer of the starting material was not observed as unreacted starting material; therefore, it is likely that isomerization to the E -oxime isomer occurs with isomerization of the allyl group to the vinyl group.
  • 61
    • 77952368171 scopus 로고    scopus 로고
    • note
    • For examples of cascade processes involving the Stetter reaction or oxidative enolate coupling with the Paal-Knorr reaction, see
  • 67
    • 77952354405 scopus 로고    scopus 로고
    • note
    • E: Z mixtures of the O -vinyl oximes were used for the synthesis of pyrroles.
  • 68
    • 77952332231 scopus 로고    scopus 로고
    • note
    • Less than 5% of 2 and the corresponding ketone were isolated with the pyrrole products. The remainder of the starting material is most likely converted into a highly colored polymeric material that remains physisorbed to silica gel.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.