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Volumn , Issue 14, 2006, Pages 2231-2234

A palladium-catalyzed sequence of allylic alkylation and Hiyama cross-coupling: Convenient synthesis of 4-(α-styryl) γ-lactones

Author keywords

Allylic alkylations; Hiyama cross coupling; Lactones; Palladium; Ring closure

Indexed keywords

4 (ALPHA STYRYL)GAMMA LACTONE; 4 [DIMETHYL (2 THIENYL)SILYLVINYL]LACTONE; ALLYL COMPOUND; GAMMA LACTONE DERIVATIVE; PALLADIUM; SILICON; UNCLASSIFIED DRUG;

EID: 33748683749     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949651     Document Type: Article
Times cited : (13)

References (31)
  • 3
    • 0003536850 scopus 로고
    • Pergamon Press: Oxford
    • Esters are known to prefer the s-trans conformation which does not possess the correct geometry for cyclization. See: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1984.
    • (1984) Stereoelectronic Effects in Organic Chemistry
    • Deslongchamps, P.1
  • 7
    • 31944443083 scopus 로고    scopus 로고
    • 3-allyl complex. In this case, the Pd-catalyzed cleavage of the malonyl moiety from the substrate might take place either before or after the C-C bond formation. See also: Silvestri, M. A.; He, C.; Khoram, A.; Lepore, S. D. Tetrahedron Lett. 2006, 47, 1625.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 1625
    • Silvestri, M.A.1    He, C.2    Khoram, A.3    Lepore, S.D.4
  • 13
    • 33748688335 scopus 로고    scopus 로고
    • note
    • 3Si group to be almost orthogonal to the C=C, whereas the distal allylic C-O bond is not expected to suffer such a restriction. Since the oxidative addition of Pd(0) to allylic acetates is known to be operative only if the substrate can adopt an orthogonal C=C/C-O disposition (ref. 7b) it appears that the silylated substrates 6 might be intrinsically biased to expel the vicinal rather than the distal allylic leaving group.
  • 15
    • 33748705475 scopus 로고    scopus 로고
    • note
    • Substrates 6a-c were easily prepared in a few steps starting from butyn-1,4-diol.
  • 16
    • 33748698348 scopus 로고    scopus 로고
    • note
    • 1H NMR of the crude products as well as TLC analysis indicate complete disappearance of the starting material and the absence of other possible regio- or stereoisomers of 7. Partial decomposition of the starting material as polymeric material is thus likely.
  • 17
    • 33748703208 scopus 로고    scopus 로고
    • note
    • 4Si: 285.1522; found: 285.1523.
  • 26
    • 33748677826 scopus 로고    scopus 로고
    • Dietrich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chap. 2
    • (c) Suzuki, A. In Metal-Catalysed Cross-Coupling Reactions; Dietrich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 2.
    • (1998) Metal-Catalysed Cross-Coupling Reactions
    • Suzuki, A.1
  • 28
    • 33748702200 scopus 로고    scopus 로고
    • note
    • 2 and the resulting organic layer was washed with brine and dried. Removal of the solvent under reduced pressure gave the crude products 10a-g, which were purified via flash chromatography.
  • 29
    • 33748714443 scopus 로고    scopus 로고
    • note
    • Hiyama couplings involving 1,2-disubstituted vinylsilanes do not show the same trend. See for example ref. 12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.