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Volumn 60, Issue 9, 2004, Pages 2097-2110

Highly diastereoselective conjugate additions of monoorganocopper reagents to chiral imides

Author keywords

1,4 Addition; Asymmetric addition; Conjugate addition; Organocopper; TMSI

Indexed keywords

AMIDE; COPPER DERIVATIVE; CROWN ETHER DERIVATIVE; IMIDE; IODOTRIMETHYLSILANE; LITHIUM DERIVATIVE; N ENOYL AMIDE; REAGENT; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1042287062     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.12.049     Document Type: Article
Times cited : (42)

References (85)
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    • Presence of iodide ions is important for transfer of the 'R' group in 'RCu' see: (b)
    • Presence of iodide ions is important for transfer of the 'R' group in 'RCu' see: (b) House H.O., Fischer W.F. J. Org. Chem. 33:1968;949-956.
    • (1968) J. Org. Chem. , vol.33 , pp. 949-956
    • House, H.O.1    Fischer, W.F.2
  • 54
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    • For a discussion on the stability of CuI/DMS complex, see:
    • For a discussion on the stability of CuI/DMS complex, see: Eriksson M., Hjelmencrantz A., Nilsson M., Olsson T. Tetrahedron. 51:1995;12631-12644.
    • (1995) Tetrahedron , vol.51 , pp. 12631-12644
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  • 55
    • 85030911360 scopus 로고    scopus 로고
    • A four month old sample of CuI·0.75DMS taken from a light-protected bottle, gave identical yields and stereoselectivities in the 1,4-additions as a freshly prepared sample of CuI·0.75DMS
    • A four month old sample of CuI·0.75DMS taken from a light-protected bottle, gave identical yields and stereoselectivities in the 1,4-additions as a freshly prepared sample of CuI·0.75DMS.
  • 60
    • 85030909333 scopus 로고    scopus 로고
    • Stoichiometry determined with elemental analysis
    • Stoichiometry determined with elemental analysis.
  • 66
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    • Lithium ion solvation energies and bond lengths have been reported: Li-carbonyl (1.746 Å), Li-THF (1.798 Å), and Li-ether (1.807 Å); see:
    • Lithium ion solvation energies and bond lengths have been reported: Li-carbonyl (1.746 Å), Li-THF (1.798 Å), and Li-ether (1.807 Å); see: Jarek R.L., Miles T.D., Trester M.L., Denson S.C., Shin S.K. J. Phys. Chem. A. 104:2000;2230-2237.
    • (2000) J. Phys. Chem. a , vol.104 , pp. 2230-2237
    • Jarek, R.L.1    Miles, T.D.2    Trester, M.L.3    Denson, S.C.4    Shin, S.K.5
  • 68
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    • 3N is added; see: Ref. 21a
    • 3N is added; see: Ref. 21a.
  • 69
  • 70
    • 0030861104 scopus 로고    scopus 로고
    • THF is an exceptional ligand for lithium ions; see: (a)
    • THF is an exceptional ligand for lithium ions; see: (a) Remenar J.F., Lucht B.L., Collum D.B. J. Am. Chem. Soc. 119:1997;5567-5572.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5567-5572
    • Remenar, J.F.1    Lucht, B.L.2    Collum, D.B.3
  • 82
    • 85030899159 scopus 로고    scopus 로고
    • 3N is added to facilitate the work-up. A basic environment prevents HI hydrolysis of the imides in aqueous media. See also footnote 24
    • 3N is added to facilitate the work-up. A basic environment prevents HI hydrolysis of the imides in aqueous media. See also footnote 24.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.