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Volumn 49, Issue 3, 2008, Pages 471-474

Catalytic enantioselective synthesis of key intermediates for NET inhibitors using atropisomeric lactam chemistry

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM; NORADRENALIN TRANSPORTER;

EID: 37349106060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.101     Document Type: Article
Times cited : (33)

References (46)
  • 5
    • 3843110770 scopus 로고    scopus 로고
    • Clayden J. (Ed)
    • In: Clayden J. (Ed). Tetrahedron symposium-in-print on axially chiral amides. Tetrahedron 60 (2004) 4325-4558
    • (2004) Tetrahedron , vol.60 , pp. 4325-4558
  • 6
    • 0026632453 scopus 로고
    • Typical examples on synthesis of optically active atropisomeric anilides and their application to asymmetric reaction:
    • Typical examples on synthesis of optically active atropisomeric anilides and their application to asymmetric reaction:. Kawamoto T., Tomishima M., Yoneda F., and Hayami J. Tetrahedron Lett. 33 (1992) 3169
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3169
    • Kawamoto, T.1    Tomishima, M.2    Yoneda, F.3    Hayami, J.4
  • 27
    • 33745438448 scopus 로고    scopus 로고
    • Papers on catalytic asymmetric synthesis of atropisomeric anilides by other groups:
    • Papers on catalytic asymmetric synthesis of atropisomeric anilides by other groups:. Brandes S., Bella M., Kjoersgaard A., and Jorgensen K.A. Angew. Chem., Int. Ed. 45 (2006) 1147
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1147
    • Brandes, S.1    Bella, M.2    Kjoersgaard, A.3    Jorgensen, K.A.4
  • 42
    • 37349017640 scopus 로고    scopus 로고
    • note
    • Interestingly, the use of (R)-DTBM-SEGPHOS which gave the best results in intermolecular reaction, was not effective in the intramolecular reaction with 1a (12% yield, 0% ee).
  • 43
    • 37349035358 scopus 로고    scopus 로고
    • note
    • Similar stereoselective α-mono-alkylation with racemic atropisomeric N-(ortho-tert-butylphenyl)-5,6-dehydropiperidin-2-one has been reported by Simpkins and co-workers (Ref. 8c).
  • 44
    • 37349007716 scopus 로고    scopus 로고
    • note
    • Stereochemistries of lactams 5a and 5a′ were determined by NOESY experiment. In 5a′, NOE between the ortho-tert-butyl group and alkenyl hydrogen was observed, while in 5a, NOE between these groups was not observed.
  • 45
    • 37349130626 scopus 로고    scopus 로고
    • note
    • 4
  • 46
    • 37349033251 scopus 로고    scopus 로고
    • note
    • 3): δ 7.50 (2H, t, J = 7.5 Hz), 7.40 (1H, t, J = 7.5 Hz), 7.16-7.20 (3H, m), 7.03 (1H, dt, J = 1.5, 7.5 Hz), 6.98 (1H, dt, J = 1.0, 7.5 Hz), 6.28...


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.