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Volumn 11, Issue 18, 2005, Pages 5408-5418

A new protocol for the consecutive α- and β-activation of propiolates towards electrophiles, involving conjugate addition of tertiary amines and intramolecular silyl migration

Author keywords

Alkynes; Domino; Formylcoumarins; Reactions; Silyl migration; Tertiary amines

Indexed keywords

ACTIVATION ANALYSIS; AMINES; HYDROCARBONS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 24644479084     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500175     Document Type: Article
Times cited : (23)

References (71)
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    • c) For a recent review see: E. Ciganek, Org. React. 1997, 57, 201;
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    • note
    • The 2D NMR spectra (HMQC and HMBC) were measured for the product 2 f (Table 3), and peak assignments were unambiguously carried out for the compound.
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    • Reviews on the nature and reactivity of alkylidenecarbenes: a) P. J. Stang, Acc. Chem. Res. 1982, 15, 348;
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    • Stang, P.J.1
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    • note
    • This compound was prepared by a different method (see the Experimental Section).
  • 50
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    • note
    • We confirmed the stability of the alkyne 4n under the reaction conditions. The instability of 4d under basic conditions may be attributed to the relatively high acidity of the benzylic proton. In case of 4n, on the other hand, such deprotonation-decomposition reactions would be impeded by the influence of the two ortho substituents.
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    • note
    • The yields were calculated based on the amount of consumed salicylaldehyde. Remaining salicylaldehyde could be removed simply by alkaline extraction: see the Experimental Section.
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    • 0002542171 scopus 로고
    • Conversion of acylsilanes into silyloxycarbenes by thermal rear-rangement, and subsequent transformations have been reported see: A. R. Bassindale, A. G. Brook, J. Harris, J. Organomet. Chem. 1975, 90, C6.
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    • Bassindale, A.R.1    Brook, A.G.2    Harris, J.3
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    • Compound 17 was synthesized from coumarin-3-carboxylic acid by the Pd-catalyzed reaction according to the reported procedure: K. Yamamoto, S. Suzuki, J. Tsuji, Tetrahedron Lett. 1980, 21, 1653.
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    • Yamamoto, K.1    Suzuki, S.2    Tsuji, J.3
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    • 24644493643 scopus 로고    scopus 로고
    • note
    • The preparative method for the deuterated salicylaldehyde was described in the Experimental Section.
  • 66
    • 24644470851 scopus 로고    scopus 로고
    • note
    • 1 H NMR spectroscopy.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.