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Volumn 348, Issue 16-17, 2006, Pages 2466-2474

Asymmetric catalysis in the [2 + 2 + 2] cycloaddition of arynes and alkynes: Enantioselective synthesis of a pentahelicene

Author keywords

2+2+2 cycloaddition; Arynes; Asymmetric catalysis; Helicenes; Palladium

Indexed keywords


EID: 33845238286     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600319     Document Type: Article
Times cited : (89)

References (61)
  • 35
    • 33845259116 scopus 로고    scopus 로고
    • MacSpartan Plus; Wavefunction, Inc.; 18401 Von Karman Ave., #370, Irvine, CA 92715
    • MacSpartan Plus; Wavefunction, Inc.; 18401 Von Karman Ave., #370, Irvine, CA 92715.
  • 39
    • 33845275715 scopus 로고    scopus 로고
    • note
    • To obtain the DFT racemization barrier, a single point calculation was carried out using the major basis set 6-311+ + G(d,p) at the 6-31G(d,p) geometry. The thermal contribution to free energy was estimated at the AM1 level.
  • 40
    • 33845261479 scopus 로고    scopus 로고
    • note
    • [27]
  • 41
    • 33845236315 scopus 로고    scopus 로고
    • note
    • Previous analysis of racemic 1 by chiral HPLC showed two resolved peaks of equal areas and identical UV spectra, corresponding to both enantiomers of pentahelicene 1.
  • 44
    • 33845238187 scopus 로고    scopus 로고
    • note
    • 3 with (R)-BINAP in CH3́CN/THF (1.5:1) for 7 h at room temperature, affords quantitative formation of 9 (NMR, TLC).
  • 45
    • 33845273742 scopus 로고    scopus 로고
    • note
    • 3 with (R)-BINAP for 1 h, led to identical results that those obtained when the catalyst 9 was isolated before use.
  • 53
    • 33845238613 scopus 로고    scopus 로고
    • note
    • A very slow addition rate of the TBAF solution is required. Otherwise, the fast generation of the aryne leds to low yields of the [2 + 2 + 2] cycloaddition products.
  • 54
    • 33845255697 scopus 로고    scopus 로고
    • note
    • 1 × t.
  • 55
    • 33845265802 scopus 로고    scopus 로고
    • note
    • 2/(S)-(-)-BPO- catalyzed cycloisomerization of an aromatic triyne.
  • 56
    • 0028039221 scopus 로고
    • Previous reports on catalytic enantioselective [2 + 2+2] cycloadditions: a) Y. Sato, T. Nishimata, M. Mon J. Org. Chem. 1994, 59, 6133-6135;
    • (1994) J. Org. Chem. , vol.59 , pp. 6133-6135
    • Sato, Y.1    Nishimata, T.2    Mon, M.3
  • 58
    • 0026724082 scopus 로고
    • Column OL-86 was prepared in the laboratories of Prof. Dr. Cristina Minguillón (Universitat de Barcelona) using the chiral selector of column CSP-1c. See: L. Oliveros, C. Minguillón, B. Desmazieres, P.-L. Besbene, J. Chromatogr. A 1992, 606, 9-17.
    • (1992) J. Chromatogr. A , vol.606 , pp. 9-17
    • Oliveros, L.1    Minguillón, C.2    Desmazieres, B.3    Besbene, P.-L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.