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Volumn 70, Issue 16, 2005, Pages 6282-6290

Preparation of carbocycles via base-catalyzed endo-mode cyclization of allenes

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; NITROGEN COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS;

EID: 23044509550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050729w     Document Type: Article
Times cited : (22)

References (59)
  • 2
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    • Chem. Abstr. 1988, 109, 22316d.
    • (1988) Chem. Abstr. , vol.109
  • 21
    • 22944443399 scopus 로고    scopus 로고
    • Krause, N., Stephen, A., Hashmi, K., Eds.; Wiley-VCH: Weinheim
    • Ma, S. In Modern Allene Chemistry; Krause, N., Stephen, A., Hashmi, K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 595-684.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 595-684
    • Ma, S.1
  • 22
    • 37049087954 scopus 로고
    • Parsons and co-workers reported the intramolecular Michael-type reaction of allene derivative with a terminal carbanion species. Thus, the ring-closing reaction of dimethyl 4-methyl-6-(phenylsulfinyl)-4,5-hexadiene-1,1-dicarboxylate resulted in the formation of seven-membered oxacycles, instead of the expected carbocycles, presumably due to exo-mode closure by the oxygen atom of the methoxycarbonyl moiety at the sp-hybridized carbon center. The cyclopentane derivative, which would be anticipated by the attack of the terminal carbanion moiety in an exo-mode manner, could not be detected. Pairaudeau, G.; Parsons, P. J.; Underwood, J. M. Chem. Commun. 1987, 1718-1720.
    • (1987) Chem. Commun. , pp. 1718-1720
    • Pairaudeau, G.1    Parsons, P.J.2    Underwood, J.M.3
  • 24
    • 0037148995 scopus 로고    scopus 로고
    • The intermolecular Michael-type reaction between the 1,2-allenyl ketones with the active methine derivatives has been reported. Ma, S.; Yin, S.; Li, L.; Tao, F. Org. Lett. 2002, 4, 505-507.
    • (2002) Org. Lett. , vol.4 , pp. 505-507
    • Ma, S.1    Yin, S.2    Li, L.3    Tao, F.4
  • 32
    • 0032497686 scopus 로고    scopus 로고
    • Dai described an exo-mode ring-closing reaction of allenyl sulfones resulting in the formation of five-membered oxacycles: Dai, W.-M.; Lee, M. Y. H. Tetrahedron 1998, 54, 12497-12512.
    • (1998) Tetrahedron , vol.54 , pp. 12497-12512
    • Dai, W.-M.1    Lee, M.Y.H.2
  • 34
    • 0000450013 scopus 로고    scopus 로고
    • An endo-mode ring-closing reaction of trisubstituted allenylphosphine oxides, leading to the dihydrofuran skeleton, has been reported: Pravia, K.; White, R.; Fodda, R.; Maynard, D. F. J. Org. Chem. 1996, 61, 6031-6032.
    • (1996) J. Org. Chem. , vol.61 , pp. 6031-6032
    • Pravia, K.1    White, R.2    Fodda, R.3    Maynard, D.F.4
  • 35
    • 0034915899 scopus 로고    scopus 로고
    • Brel reported an exo-mode cyclization of the allenyl phosphonate derivatives leading to a furan framework: Brel, V. K. Synthesis 2001, 1539-1545.
    • (2001) Synthesis , pp. 1539-1545
    • Brel, V.K.1
  • 37
    • 0037450464 scopus 로고    scopus 로고
    • Part of this work was published as a preliminary communication: Mukai, C.; Ukon, R.; Kuroda, N. Tetrahedron Lett. 2003, 44, 1583-1586.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1583-1586
    • Mukai, C.1    Ukon, R.2    Kuroda, N.3
  • 42
    • 33544460284 scopus 로고    scopus 로고
    • note
    • tBuOH and THF (1:1) was used for this compound due to its solubility.
  • 43
    • 33544459544 scopus 로고    scopus 로고
    • note
    • Allenes 14 were prepared from the hexynyl iodide derivatives 12 via the corresponding active methine derivatives 13 (see the Supporting Information).
  • 44
    • 33544464063 scopus 로고    scopus 로고
    • note
    • Compounds 7e and 14e were prepared according to the general procedure (see the Supporting Information).
  • 45
    • 33544466367 scopus 로고    scopus 로고
    • note
    • Compound 28 was prepared from the known dimethyl malonate derivative 26 (see the Supporting Information).
  • 46
    • 33544465376 scopus 로고    scopus 로고
    • note
    • 1H NMR spectral analysis.
  • 47
    • 33544469419 scopus 로고    scopus 로고
    • note
    • 1H NMR spectral analysis.
  • 48
    • 33544458098 scopus 로고    scopus 로고
    • note
    • Compound 29 was prepared from the known dimethyl malonate derivative 27 (see the Supporting Information).
  • 49
    • 33544461001 scopus 로고    scopus 로고
    • note
    • Allenes 39-41 were prepared from the corresponding alkynes 33-35 via compounds 36-38 (see the Supporting Information).
  • 50
    • 33544460176 scopus 로고    scopus 로고
    • note
    • The (E)-stereochemistry of 42a, 43a, and 44a was determined by an NOE experiment. For instance, 1.4% enhancement of Ha of 43a was observed upon irradiation of a vinyl proton.
  • 51
    • 33544461245 scopus 로고    scopus 로고
    • note
    • tBuOLi for 5 min.
  • 52
    • 33544469529 scopus 로고    scopus 로고
    • note
    • tBuOLi for 5 min.
  • 53
    • 33544457550 scopus 로고    scopus 로고
    • note
    • The (Z)-stereochemistry of 42b, 43b, and 44b was confirmed as follows. Treatment of 42b, for example, with DDQ afforded the allylic alcohol derivative 45 in 91% yield. An NOE experiment of 45 revealed a 9% enhancement of Ha when allylic protons were irradiated.
  • 54
    • 33544455088 scopus 로고    scopus 로고
    • note
    • Compounds 47 and 48 were obtained as a mixture of two diastereoisomers in a ratio of ca. 1:1.
  • 55
    • 33544455266 scopus 로고    scopus 로고
    • note
    • Compound 51 was prepared form the known iodobenzene derivative 49 via the propargyl alcohol derivative 50 (see the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.