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Volumn 6, Issue 13, 2004, Pages 2281-2283

Diastereoselective zinc-catalyzed conjugate addition of alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ZINC;

EID: 3142757947     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0491585     Document Type: Article
Times cited : (42)

References (39)
  • 3
    • 0001096579 scopus 로고
    • The addition of copper alkynylides to enones has been reported to proceed in the presence of activating agents such as TMSI/LiI or TBDMSOTf, see: (a) Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. (b) Kim S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783-786.
    • (1993) J. Org. Chem. , vol.58 , pp. 7238-7244
    • Bergdahl, M.1    Eriksson, M.2    Nilsson, M.3    Olsson, T.4
  • 4
    • 0001096579 scopus 로고
    • The addition of copper alkynylides to enones has been reported to proceed in the presence of activating agents such as TMSI/LiI or TBDMSOTf, see: (a) Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. (b) Kim S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783-786.
    • (1995) Bull. Korean Chem. Soc. , vol.16 , pp. 783-786
    • Kim, S.1    Park, J.H.2    Jon, S.Y.3
  • 11
    • 0034054973 scopus 로고    scopus 로고
    • Chong and co-workers have reported the use of alkynylboronates prepared from 3,3′-diphenyl-BINOL in enantioselective additions to unsaturated ketones: Chong, J. M.; Shen, L. X.; Taylor, N. J. J. Am. Chem. Soc. 2000, 122, 1822-1823.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1822-1823
    • Chong, J.M.1    Shen, L.X.2    Taylor, N.J.3
  • 30
    • 3142736432 scopus 로고    scopus 로고
    • For details see the Supporting Information
    • For details see the Supporting Information.
  • 32
    • 3142705762 scopus 로고    scopus 로고
    • note
    • 3 = tBu), see Supporting Information. The stereochemistry was initially missassigned (ref 15), but later corrected (refs 19 and 20).
  • 36
    • 0006287614 scopus 로고
    • 2 in EtOAc (quant.) and comparing the optical rotation with a reported value: Enders, D.; Rendenbach, B. E. M Tetrahedron 1986, 42, 2235-2242.
    • (1986) Tetrahedron , vol.42 , pp. 2235-2242
    • Enders, D.1    Rendenbach, B.E.M.2
  • 37
    • 3142666095 scopus 로고    scopus 로고
    • note
    • Addition of 4-phenyl-l-butyne to (E)-4d with use of 60 mol % of zinc and converting the adduct into the β-alkynyl acid gave ent-6d in 84% yield and 95% ee (not shown).
  • 38
    • 0000559897 scopus 로고
    • β substitution, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749-5759.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3128-3130
    • Schreiber, S.L.1    Sammakia, T.2    Crowe, W.E.3
  • 39
    • 0000882082 scopus 로고
    • β substitution, see: (a) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128-3130. (b) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749-5759.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5749-5759
    • Schreiber, S.L.1    Klimas, M.T.2    Sammakia, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.