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Volumn 126, Issue 10, 2004, Pages 3113-3118

Reaction of Ketones with Lithium Hexamethyldisilazide: Competitive Enolizations and 1,2-Additions

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DIMERS; INFRARED SPECTROSCOPY; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TOLUENE;

EID: 1642415874     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030582v     Document Type: Article
Times cited : (39)

References (80)
  • 6
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    • For leading references and recent examples of detectable organolithium-substrate precomplexation, see: (a) Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1.
    • (1986) Recl. Trav. Chim. Pays-Bas , vol.105 , pp. 1
    • Klumpp, G.W.1
  • 10
    • 0000964801 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: New York
    • For a general discussion of ketone-lithium complexation and related ketone-Lewis acid complexation, see: Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 1, p 283.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 283
    • Shambayati, S.1    Schreiber, S.L.2
  • 14
    • 1642340516 scopus 로고    scopus 로고
    • note
    • The concentration of the lithium amide, although expressed in units of molarity, refers to the concentration of the monomer unit (normality). The concentrations of THF and pyrrolidine are expressed as total solvent added.
  • 16
    • 1642298194 scopus 로고    scopus 로고
    • note
    • The cis and trans adducts of 3 would be formed as racemates, four stereoisomers overall. If, for example, these species formed a statistical distribution of dimers, there would be a total of six spectroscopically distinct diastereomers and a much higher number of possible tetramers. By contrast, achiral adduct 7 would likely form only one dimer and two tetramers differing by the stereochemistry of chelation. Mixed dimerization with LiHMDS as described precludes much of this complexity.
  • 26
    • 0035902858 scopus 로고    scopus 로고
    • Johansson, A.; Davidsson, O. 2001, 7, 3461. See also refs 12 and 22
    • (e) Johansson, A.; Davidsson, O. 2001, 7, 3461. See also refs 12 and 22.
  • 31
    • 1642275420 scopus 로고    scopus 로고
    • note
    • If the saturation kinetics arose from quantitative formation of lithium pyrrolidide at high pyrrolidine concentration, the rate of the 1,2-addition by LiHMDS/pyrrolidine and n-BuLi/pyrrolidine would have been equivalent.
  • 32
    • 1642386072 scopus 로고    scopus 로고
    • note
    • 2NH would have been observed.
  • 34
    • 1642381235 scopus 로고    scopus 로고
    • see ref 1b
    • For leading references to applications of LiHMDS/THF in synthesis, see ref 1b.
  • 45
    • 1642285148 scopus 로고    scopus 로고
    • See also ref 7
    • (d) See also ref 7.
  • 57
    • 0036147233 scopus 로고    scopus 로고
    • For additional leading references to synthetic applications of organolithiums solvated by protic amines see ref 32
    • Eames, J.; Weerasooriya, N.; Coumbarides, G. S. Eur. J. Org. Chem. 2002, 181. For additional leading references to synthetic applications of organolithiums solvated by protic amines, see ref 32.
    • (2002) Eur. J. Org. Chem. , vol.181
    • Eames, J.1    Weerasooriya, N.2    Coumbarides, G.S.3
  • 73
    • 1642366523 scopus 로고    scopus 로고
    • See also ref 24
    • (k) See also ref 24.
  • 74
    • 1642299798 scopus 로고    scopus 로고
    • Unpublished work
    • C-N coupling: Sun, X. ; Collum, D. B. Unpublished work.
    • Sun, X.1    Collum, D.B.2
  • 80
    • 0001720499 scopus 로고
    • For example, see: Mohrig, J. R.; Lee, P. K.; Stein, K. A.; Mitton, M. J. ; Rosenberg, R. E. J. Org. Chem. 1995, 60, 3529. For an excellent discussion and leading references, see: Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 891
    • Vedejs, E.1    Lee, N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.