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Volumn 5, Issue 15, 2007, Pages 2357-2360

Synthesis of α,β-unsaturated γ-lactams via asymmetric iridium-catalysed allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CATALYSIS; ENANTIOSELECTIVITY; IRIDIUM; SYNTHESIS (CHEMICAL);

EID: 34547208210     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b708571k     Document Type: Article
Times cited : (49)

References (34)
  • 23
    • 17444425377 scopus 로고    scopus 로고
    • Additionally, benzhydrylamine and p-methoxybenzylamine were used as nucleophiles to give allylamines with excellent enantio- and regioselectivities. The allyamines were transformed into N-(3-methylacryloyl)-amines F, which were subjected to RCM to furnish lactams G;
    • C. Welter A. Dahnz B. Brunner S. Streiff P. Dübon G. Helmchen Org. Lett. 2005 7 1239
    • (2005) Org. Lett. , vol.7 , pp. 1239
    • Welter, C.1    Dahnz, A.2    Brunner, B.3    Streiff, S.4    Dübon, P.5    Helmchen, G.6
  • 24
    • 34547150465 scopus 로고    scopus 로고
    • Universität Heidelberg
    • S. Spiess, MSc thesis, Universität Heidelberg, 2006
    • (2006)
    • Spiess Msc Thesis, S.1
  • 25
    • 34547163784 scopus 로고    scopus 로고
    • Universität Heidelberg
    • C. Berthold, MSc thesis, Universität Heidelberg, 2006
    • (2006)
    • Berthold Msc Thesis, C.1
  • 28
    • 2942594935 scopus 로고    scopus 로고
    • Diacylamides 3 are somewhat sensitive to acidic conditions. In particular, lengthy chromatographic processes using silica cause lowering of yield TBD: 1,5,7-triazabicyclo-[4.4.0]dec-5-ene For L1 ca. 2 h are optimal, while for L2 ca. 5 min are sufficient, cf.
    • K. Li X. Cheng K. K. Hii Eur. J. Org. Chem. 2004 959
    • (2004) Eur. J. Org. Chem. , pp. 959
    • Li, K.1    Cheng, X.2    Hii, K.K.3
  • 29
    • 33947728054 scopus 로고    scopus 로고
    • HPLC Data for 3 (Table 1), Daicel columns, 250 × 4.6 mm, 5 m with guard cartridge, 10 × 4 mm, 0.5 mL min-1; 3a: Chiralcel OD-H, n-hexane/i-PrOH 99.9: 0.1, rt, 220 nm, tR[(-)-(S)- 3a] = 19 min, tR[(+)-(R)- 3a] = 21 min; 3b: Chiralcel OD-H, n-hexane/i-PrOH 99.9: 0.1, rt, 220 nm, tR [3b] = 16 min and 19 min; 3c: Chiralcel AD-H, n-hexane/i-PrOH 98: 2, rt, 220 nm, tR[(+)- 3c] = 10 min, t R[(-)- 3c] = 11 min; 3d: Chiralcel OD-H, n-hexane/i-PrOH 99: 1, rt, 210 nm, tR[(+)- 3d] = 11 min, tR[(-)- 3d] = 18 min An exception is the compound 5, R = 2-furyl, which was formed with complete racemisation Several related amides F (R′ = CH3 and Σ = Bn or p-MeOC6H4) were also subjected to RCM. Double bond isomerisation was only found in the case R = n-Pr, likely caused by residual Ru compounds in the products, cf.
    • C. Gnamm S. Förster N. Miller K. Brödner G. Helmchen Synlett 2007 790
    • (2007) Synlett , pp. 790
    • Gnamm, C.1    Förster, S.2    Miller, N.3    Brödner, K.4    Helmchen, G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.