메뉴 건너뛰기




Volumn 6, Issue 20, 2004, Pages 3549-3551

Selective mono-N-alkylation of 3-amino alcohols via chelation to 9-BBN

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

EID: 6444228154     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048554k     Document Type: Article
Times cited : (15)

References (27)
  • 2
    • 0000653482 scopus 로고    scopus 로고
    • Bar Haim, G.; Kol, M. J. Org. Chem. 1997, 62, 6682. See also: Bar Haim, G.; Shach, R.; Kol, M. Chem. Commun. 1997, 229.
    • (1997) J. Org. Chem. , vol.62 , pp. 6682
    • Bar Haim, G.1    Kol, M.2
  • 4
    • 0032565849 scopus 로고    scopus 로고
    • For application of this approach in the synthesis of chiral "proton sponges", see: (a) Charmant, J. P. H.; Lloyd-Jones, G. C.; Peakman, T. M.; Woodward, R. L. Tetrahedron Lett. 1998, 39, 4733. (b) Charmant, J. P. H.; Lloyd-Jones, G. C.; Peakman, T. M.; Woodward, R. L. Eur. J. Org. Chem. 1999, 2501. (c) Lloyd-Jones, G. C. Synlett 2001, 161.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4733
    • Charmant, J.P.H.1    Lloyd-Jones, G.C.2    Peakman, T.M.3    Woodward, R.L.4
  • 5
    • 0032840169 scopus 로고    scopus 로고
    • For application of this approach in the synthesis of chiral "proton sponges", see: (a) Charmant, J. P. H.; Lloyd-Jones, G. C.; Peakman, T. M.; Woodward, R. L. Tetrahedron Lett. 1998, 39, 4733. (b) Charmant, J. P. H.; Lloyd-Jones, G. C.; Peakman, T. M.; Woodward, R. L. Eur. J. Org. Chem. 1999, 2501. (c) Lloyd-Jones, G. C. Synlett 2001, 161.
    • (1999) Eur. J. Org. Chem. , pp. 2501
    • Charmant, J.P.H.1    Lloyd-Jones, G.C.2    Peakman, T.M.3    Woodward, R.L.4
  • 6
    • 0035121607 scopus 로고    scopus 로고
    • For application of this approach in the synthesis of chiral "proton sponges", see: (a) Charmant, J. P. H.; Lloyd-Jones, G. C.; Peakman, T. M.; Woodward, R. L. Tetrahedron Lett. 1998, 39, 4733. (b) Charmant, J. P. H.; Lloyd-Jones, G. C.; Peakman, T. M.; Woodward, R. L. Eur. J. Org. Chem. 1999, 2501. (c) Lloyd-Jones, G. C. Synlett 2001, 161.
    • (2001) Synlett , pp. 161
    • Lloyd-Jones, G.C.1
  • 10
    • 0141677864 scopus 로고    scopus 로고
    • For selective monomethylation of substituted anilines by dimethyl carbonate in the presence of a zeolite catalyst, see: Selva, M.; Tundo, P.; Perosa, A. J. Org. Chem. 2003, 68, 7374.
    • (2003) J. Org. Chem. , vol.68 , pp. 7374
    • Selva, M.1    Tundo, P.2    Perosa, A.3
  • 25
    • 33847088937 scopus 로고
    • Parent compound, 2-aminoethanol, is known to form a five-membered chelate with 9-BBN: (a) Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1977, 42, 1197. (b) Brown, H. C.; Prasad, J. V. N. V. J. Org. Chem. 1986, 57, 4526.
    • (1977) J. Org. Chem. , vol.42 , pp. 1197
    • Krishnamurthy, S.1    Brown, H.C.2
  • 26
    • 33847088937 scopus 로고
    • Parent compound, 2-aminoethanol, is known to form a five-membered chelate with 9-BBN: (a) Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1977, 42, 1197. (b) Brown, H. C.; Prasad, J. V. N. V. J. Org. Chem. 1986, 57, 4526.
    • (1986) J. Org. Chem. , vol.57 , pp. 4526
    • Brown, H.C.1    Prasad, J.V.N.V.2
  • 27
    • 6444231640 scopus 로고    scopus 로고
    • note
    • Attempted extension of this methodology to secondary alkyl halides (e.g., isopropyl bromide) failed, apparently due to a competing elimination reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.