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Volumn , Issue 24, 2006, Pages 2607-2609

Reactivity series for s-BuLi/diamine-mediated lithiation of N-Boc pyrrolidine: Applications in catalysis and lithiation of N-Boc piperidine

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; DIAMINE DERIVATIVE; LIGAND; PIPERIDINE; PYRROLIDINE DERIVATIVE; SPARTEINE;

EID: 33745224132     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b603804m     Document Type: Article
Times cited : (64)

References (34)
  • 3
    • 33645317246 scopus 로고    scopus 로고
    • The Chemistry of Organolithium Compounds. in
    • Z. Rappoport and I. Marek, Wiley, Chichester, 997
    • R. E. Gawley and I. Coldham, The Chemistry of Organolithium Compounds. In The Chemistry of Functional Groups, ed., Z. Rappoport, and, I. Marek,, Wiley, Chichester, 2004, 997
    • (2004) The Chemistry of Functional Groups, Ed.
    • Gawley, R.E.1    Coldham, I.2
  • 4
    • 0037503118 scopus 로고    scopus 로고
    • The Chemistry of Organolithium Compounds, in
    • Z. Rappoport and I. Marek, Wiley, Chichester, 1077
    • D. Hoppe and G. Christoph, The Chemistry of Organolithium Compounds, in The Chemistry of Functional Groups, ed., Z. Rappoport, and, I. Marek,, Wiley, Chichester, 2004, 1077
    • (2004) The Chemistry of Functional Groups, Ed.
    • Hoppe, D.1    Christoph, G.2
  • 28
    • 33745210686 scopus 로고    scopus 로고
    • 3SiCl was added and it was found that ∼26% (by GC) of (S)-4 of 98 : 2 er had been generated
    • 3SiCl was added and it was found that ∼26% (by GC) of (S)-4 of 98 : 2 er had been generated
  • 29
    • 33745211127 scopus 로고    scopus 로고
    • This result also suggests that ligand exchange catalysis (see ref. 25) is occurring to some extent, with the less reactive s-BuLi/(-)-sparteine as the regenerating system
    • This result also suggests that ligand exchange catalysis (see ref. 25) is occurring to some extent, with the less reactive s-BuLi/(-)-sparteine as the regenerating system
  • 30
    • 33745213030 scopus 로고    scopus 로고
    • This reactivity order should be treated as a guide for use in synthesis as it assumes that essentially all of each diamine is complexed to the s-BuLi
    • This reactivity order should be treated as a guide for use in synthesis as it assumes that essentially all of each diamine is complexed to the s-BuLi
  • 32
    • 33751385209 scopus 로고
    • A similar reactivity difference between s-BuLi/TMEDA and s-BuLi/(-)-sparteine was noted in the lithiation of a N-Boc bispidine:
    • P. Beak W. K. Lee J. Org. Chem. 1993 58 1109
    • (1993) J. Org. Chem. , vol.58 , pp. 1109
    • Beak, P.1    Lee, W.K.2
  • 33
    • 0034609185 scopus 로고    scopus 로고
    • Er determined by chiral HPLC on the p-bromobenzamide of 12 or by chiral GC. Absolute configuration assigned by analogy with the (R)-N-Boc stannane which was transformed into the known (R)-N-Me stannane. For the (S)-N-Me stannane, see:
    • J. R. Harrison P. O'Brien Tetrahedron Lett. 2000 41 6161
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6161
    • Harrison, J.R.1    O'Brien, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.