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Volumn 127, Issue 49, 2005, Pages 17168-17169

Catalytic enantioselective conia-ene reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBONYL DERIVATIVE; KETONE;

EID: 29044442544     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055059q     Document Type: Article
Times cited : (193)

References (36)
  • 5
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    • (e) Fuji, K. Chem. Rev. 1993, 93, 2037.
    • (1993) Chem. Rev. , vol.93 , pp. 2037
    • Fuji, K.1
  • 6
    • 0037174368 scopus 로고    scopus 로고
    • For recent examples of enantioselective intermolecular Michael of prochiral pronucleophiles, see: (a) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11240
    • Hamashima, Y.1    Hotta, D.2    Sodeoka, M.3
  • 18
    • 4644230134 scopus 로고    scopus 로고
    • For Pd-catalyzed α-allylation of ketoesters using alkynes. see: (b) Yamamoto, Y.; Patil, N. T. J. Org. Chem. 2004, 69, 6478.
    • (2004) J. Org. Chem. , vol.69 , pp. 6478
    • Yamamoto, Y.1    Patil, N.T.2
  • 21
    • 29044445264 scopus 로고    scopus 로고
    • For an enantioselective cycloaddition of an alkyne see: (c) Shintani, R.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 10788.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10788
    • Shintani, R.1    Fu, G.C.2
  • 24
    • 29044433124 scopus 로고    scopus 로고
    • note
    • 8 (<5% ee) and BINAP-platinum(II) (18% ee) complexes promoted the reaction: however, the enantioselectivity was poor.
  • 32
    • 10044289642 scopus 로고    scopus 로고
    • Addition of β-dicarbonyl compounds to olefins catalyzed by Pt(II), Eu(III) and stoichiometric HCl, see: Liu, C.; Widenhoefer, R. A. Tetrahedron Lett. 2005, 46, 285.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 285
    • Liu, C.1    Widenhoefer, R.A.2
  • 33
    • 29044438333 scopus 로고    scopus 로고
    • note
    • 6b required prolonged reaction times (7 days) and gave racemic products.
  • 34
    • 29044440157 scopus 로고    scopus 로고
    • note
    • In accord with a mechanism involving Irans addition to the alkyne, cyclization of a deutero-acetylene resulted in isolation of the adduct in which deuterium was only incorporated cis to the ketoester; however, this experiment was complicated by deuterium exchange of acetylenic proton.
  • 35
    • 1942533585 scopus 로고    scopus 로고
    • A mechanism involving alkyne activation by Pd(II) was excluded in isomerization of 1,6-enynes catalyzed by related cationic bis(phosphine)- palladium(II) complexes: Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5767.
    • (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 5767
    • Mikami, K.1    Hatano, M.2
  • 36
    • 29044436117 scopus 로고    scopus 로고
    • note
    • 2a


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.