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Volumn 7, Issue 18, 2005, Pages 3905-3908

Reactions of (Trialkylsilyl)vinylketenes with lithium ynolates: A new benzannulation strategy

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; LITHIUM; ORGANOSILICON DERIVATIVE;

EID: 24944514432     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051307b     Document Type: Article
Times cited : (54)

References (44)
  • 1
    • 0003828015 scopus 로고
    • Wiley: New York
    • ) Reviewed in: Tidwell, T. T. Ketenes; Wiley: New York, 1995.
    • (1995) Ketenes
    • Tidwell, T.T.1
  • 23
    • 0242656295 scopus 로고    scopus 로고
    • For reviews of the chemistry of ynolates. see: (a) Shindo, M. Synthesis 2003, 2275.
    • (2003) Synthesis , pp. 2275
    • Shindo, M.1
  • 28
    • 33845554701 scopus 로고
    • Siloxy alkyne 9c (see Supporting Information) was prepared using a two-step variant of the Kowalski reaction; see: (a) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 321
    • Kowalski, C.J.1    Fields, K.W.2
  • 30
    • 24944580000 scopus 로고    scopus 로고
    • note
    • The possibility that intermediate 11 might form via a concerted [4 + 2] cycloaddition of 1 and TAS-vinylketene 2 cannot be excluded.
  • 31
    • 0011847933 scopus 로고
    • For a discussion of the 6π electrocyclization of 3-oxido-1,3,5- hexatrienes, see: Magnus, P. Nouv. J. Chem. 1978, 2, 555.
    • (1978) Nouv. J. Chem. , vol.2 , pp. 555
    • Magnus, P.1
  • 32
    • 24944446013 scopus 로고
    • For prior examples of 6π electrocyclization reactions involving enolate derivatives, see: (a) White, J. D.; Skeean, R. W. J. Am. Chem. Soc. 1978, 100, 6296.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 6296
    • White, J.D.1    Skeean, R.W.2
  • 36
    • 0033595558 scopus 로고    scopus 로고
    • For a recent theoretical study and leading references, see: Takahashi, M.; Kira, M. J. Am. Chem. Soc. 1999, 121, 8597.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8597
    • Takahashi, M.1    Kira, M.2
  • 41
    • 84991182227 scopus 로고
    • The metalation of 1-phenyl-4-penten-1-yne with MeLi has previously been reported: Klein, J.; Brenner, S.; Medlik, A. Isr. J. Chem. 1971, 9, 177.
    • (1971) Isr. J. Chem. , vol.9 , pp. 177
    • Klein, J.1    Brenner, S.2    Medlik, A.3
  • 42
    • 24944457247 scopus 로고    scopus 로고
    • see Supporting Information
    • The TBDMS siloxy alkyne 23 was prepared from allylacetylene by employing the method of Julia (see Supporting Information). In general, however, the use of TIPS derivatives is preferred because of their increased stability to purification and storage.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.