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Volumn 12, Issue 17, 2010, Pages 3780-3783

Copper-catalyzed Ficini [2 + 2] cycloaddition of ynamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; COPPER; SULFONE;

EID: 77956208395     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101418d     Document Type: Article
Times cited : (60)

References (61)
  • 1
    • 77956215910 scopus 로고    scopus 로고
    • For a seminal review on Ficini [2 + 2] cycloaddition using ynamines, see
    • For a seminal review on Ficini [2 + 2] cycloaddition using ynamines, see
  • 3
    • 77956224179 scopus 로고    scopus 로고
    • For two other comprehensive reviews on ynamine chemistry, see
    • For two other comprehensive reviews on ynamine chemistry, see
  • 6
    • 77956215629 scopus 로고    scopus 로고
    • For a review on thermal [2 + 2] cycloaddition reactions, see
    • For a review on thermal [2 + 2] cycloaddition reactions, see
  • 7
    • 0002648396 scopus 로고
    • Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon Press: New York
    • Baldwin, J. E. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 63.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 63
    • Baldwin, J.E.1
  • 13
    • 77956216258 scopus 로고    scopus 로고
    • For cycloadditions to quinone, see
    • For cycloadditions to quinone, see
  • 15
    • 77956217997 scopus 로고    scopus 로고
    • For related examples that were contemporary, see
    • For related examples that were contemporary, see
  • 19
    • 77956194670 scopus 로고    scopus 로고
    • For Ficini s later work, see
    • For Ficini s later work, see
  • 22
    • 77956223665 scopus 로고    scopus 로고
    • For comprehensive reviews on chemistry of ynamides, see
    • For comprehensive reviews on chemistry of ynamides, see
  • 25
    • 77956214284 scopus 로고    scopus 로고
    • For recent examples, see
    • For recent examples, see
  • 42
    • 84855625629 scopus 로고    scopus 로고
    • 2, see
    • 2, see
  • 45
    • 77956206339 scopus 로고    scopus 로고
    • note
    • 2 in general because of the overall stability difference between the respective conjugate bases [as one referee kindly pointed out], sulfonyl-substituted ynamides [or enamides] are more reactive and less stable than simple amide or urethane-substituted ynamides [or enamide]. The nitrogen lone pair in the former is more delocalized into the alkyne [or alkene motif] and more into the carbonyl group in the latter. Likewise, but in a reverse sense, for iminium ion chemistry, sulfonyl-substituted iminium species are more stable and less reactive than straight N-acyl iminium ions because the nitrogen lone pair in the former is more involved in the π-donation to the carbocation. See
  • 48
    • 77956207383 scopus 로고    scopus 로고
    • note
    • For α-halogenations of ynamides observed using Pd(0) and Rh(I), see
  • 51
    • 77956210127 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 55
    • 77956222619 scopus 로고    scopus 로고
    • note
    • Conjugation appears to be a key, as cyclohexenyl methyl ketone did not give i when reacted with ynamide 12. On the other hand, cyclohexenyl nitrile gave a completely different product pyrimidine iii, thereby suggesting a cyclotrimerization process. Regiochemistry of iii was assigned using NOE [see Supporting Information ].
  • 57
    • 77956209461 scopus 로고    scopus 로고
    • note
    • Keto-imide 31 could be further hydrolyzed to 30-syn and 30-anti in 1:1 ratio using the same conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.