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Volumn 128, Issue 5, 2006, Pages 1406-1407

Palladium(0)-catalyzed alkylative cyclization of alkynals and alkynones: Remarkable trans-addition of organoboronic reagents

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; KETONE DERIVATIVE; ORGANOBORON DERIVATIVE; PALLADIUM; REAGENT;

EID: 32244433731     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056458o     Document Type: Article
Times cited : (68)

References (27)
  • 3
    • 4544323639 scopus 로고    scopus 로고
    • (c) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890 and references therein. For the synthesis of allylamines, see:
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3890
    • Montgomery, J.1
  • 11
    • 2942702050 scopus 로고    scopus 로고
    • We recently reported the palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with arylboronic acids. Tsukamoto, H.; Sato, M.; Kondo, Y. Chem. Commun. 2004, 1200.
    • (2004) Chem. Commun. , pp. 1200
    • Tsukamoto, H.1    Sato, M.2    Kondo, Y.3
  • 14
    • 84989456545 scopus 로고
    • Some examples of trans-selective carbometalation of functionalized alkynes are reported, (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841.
    • (1981) Synthesis , pp. 841
    • Normant, J.F.1    Alexakis, A.2
  • 15
    • 0035833014 scopus 로고    scopus 로고
    • and references therein
    • (b) Fallis, A. G.; Forgoine, P. Tetrahedron 2001, 57, 5899 and references therein.
    • (2001) Tetrahedron , vol.57 , pp. 5899
    • Fallis, A.G.1    Forgoine, P.2
  • 16
    • 0003059123 scopus 로고
    • Palladium catalysts have not been employed previously because they are less suitable for insertion into carbonyl groups. The limited number of palladium-catalyzed carbonyl alkenylations are based on carbonyl insertions into organopalladium(II) formed in situ, (a) Vicente, J.; Abad, J.-A.; Gil-Rubio, J. J. Organomet. Chem. 1992, 436, C9.
    • (1992) J. Organomet. Chem. , vol.436
    • Vicente, J.1    Abad, J.-A.2    Gil-Rubio, J.3
  • 22
    • 32244440447 scopus 로고    scopus 로고
    • note
    • Structure determinations were performed by using NOESY techniques, transformations into the known compounds, and preparations of authentic samples; see Supporting Information.
  • 24
    • 32244437290 scopus 로고    scopus 로고
    • note
    • Alkylboronic acids are not suitable as nucleophiles.
  • 25
    • 0037016947 scopus 로고    scopus 로고
    • An "anti-Wacker"-type mechanism was proposed for hydroalkoxylation of electron-deficient alkenes and alkynes. See: (a) Camacho, D. H.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 1085.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1085
    • Camacho, D.H.1    Saito, S.2    Yamamoto, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.