메뉴 건너뛰기




Volumn 350, Issue 2, 2008, Pages 243-248

Tandem gold(III)-catalyzed amination-intramolecular hydroamination reactions of 1-En-4-yn-3-ols with sulfonamides: Efficient approach to highly substituted pyrroles

Author keywords

1 en 4 yn 3 ols; Amination; Gold; Hydroamination; Pyrroles

Indexed keywords


EID: 38849143246     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700452     Document Type: Article
Times cited : (78)

References (74)
  • 1
    • 0001426611 scopus 로고    scopus 로고
    • Eds, A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Pergamon, Oxford
    • a) R. J. Sundberg, in: Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, Vol. 2, pp 119-206;
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 119-206
    • Sundberg, R.J.1
  • 6
    • 17744417463 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3582-3603.
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3582-3603
  • 13
    • 0033523663 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 2896-2899.
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 2896-2899
  • 14
    • 22744450570 scopus 로고    scopus 로고
    • For a review, see: a
    • For a review, see: a) G. Balme, Angew. Chem. 2004, 116, 6396-6399;
    • (2004) Angew. Chem , vol.116 , pp. 6396-6399
    • Balme, G.1
  • 15
    • 11144250168 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 6238-6241;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 6238-6241
  • 17
    • 0038112039 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 2681-2684;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 2681-2684
  • 25
    • 0000817646 scopus 로고    scopus 로고
    • For selected reviews on gold-catalyzed reactions, see: a
    • For selected reviews on gold-catalyzed reactions, see: a) G. Dyker, Angew. Chem. 2000, 112, 4407-4409:
    • (2000) Angew. Chem , vol.112 , pp. 4407-4409
    • Dyker, G.1
  • 26
    • 0034605865 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 4237-4239;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 4237-4239
  • 30
    • 13744249187 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 850-852;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 850-852
  • 32
    • 27744595601 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6990-6993;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6990-6993
  • 34
    • 33845546747 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7896-7936
  • 37
    • 0002913891 scopus 로고
    • For gold-catalyzed inter- or intramolecular hydroamination of unsaturated compounds, see, a
    • For gold-catalyzed inter- or intramolecular hydroamination of unsaturated compounds, see : a) Y. Fukuda, K. Utimoto, H. Nozaki, Heterocycles 1987, 25, 297-300;
    • (1987) Heterocycles , vol.25 , pp. 297-300
    • Fukuda, Y.1    Utimoto, K.2    Nozaki, H.3
  • 40
    • 33745716289 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1744-1747;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1744-1747
  • 42
    • 33746094780 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1747-1749;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1747-1749
  • 44
    • 33744546269 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3314-3317;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3314-3317
  • 46
    • 33750613418 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7075-7078;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 7075-7078
  • 56
    • 26844516744 scopus 로고    scopus 로고
    • Gold catalysts act as propargylic alcohol-activating agents in propargylic substitutions, see
    • Gold catalysts act as propargylic alcohol-activating agents in propargylic substitutions, see: M. Georgy, V. Boucard, J. M. Campagne, J. Am. Chem. Soc. 2005, 127, 14180-14181.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 14180-14181
    • Georgy, M.1    Boucard, V.2    Campagne, J.M.3
  • 57
    • 0035967754 scopus 로고    scopus 로고
    • N2′-like nucleophilic attack may be involved in the process. For a series of research works concerned with this system, see : a T Ishikawa, M. Okano, T. Aikawa, S. Saito, J. Org. Chem. 2001, 66, 4635-4642;
    • N2′-like nucleophilic attack may be involved in the process. For a series of research works concerned with this system, see : a) T Ishikawa, M. Okano, T. Aikawa, S. Saito, J. Org. Chem. 2001, 66, 4635-4642;
  • 62
    • 38849150747 scopus 로고    scopus 로고
    • Most of starting material was decomposed especially for Ij
    • Most of starting material was decomposed especially for Ij.
  • 63
    • 38849150096 scopus 로고    scopus 로고
    • The molecular structure of the corresponding product 3n was determined by X-ray crystallography (Figure 1, X-ray data for compound 3n: C 29H29NO2S, MW, 455.59, T= 273(2) K, γ, 0.71073 Å, monoclinic space group, P21/c, a, 8.6485(10) Å, b, 32,699(3) Å, C, 9.0126(12) Å, α, 90°, β, 109.287(2)°, γ, 90°, V= 2405.7(5) Å3 Z, 4, ρcald, 1.258 mg m-3, μ, 0.161 mm-1, F(000, 968, crystal size 0.58 × 0.54 × 0.49 mm3, independent reflections 4235 [R(int, 0.0190, reflections collected 12226, refinement method, full-matrix least-squares on F2, goodness-of-fit on F2 1.015, final R indices [1>2σ(I, R1, 0.0437, wR2, 0.1278, R indices (all date) R1, 0.0489, wR2, 0.1318, largest diff. peak and
    • -3. Supplementary crystallography data have been deposited at the Cambridge Crystallographic Data Centre: CCDC 660656.
  • 70
    • 38849124593 scopus 로고    scopus 로고
    • 18 % of pyrrole 3a was also separated.
    • 18 % of pyrrole 3a was also separated.
  • 73
    • 0034600902 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 2285-2288
  • 74
    • 38849102732 scopus 로고    scopus 로고
    • [9g]
    • [9g]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.