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Volumn 8, Issue 15, 2010, Pages 3418-3425

A three-step tandem process for the synthesis of bicyclic γ-lactams

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ONE POT; OVERMAN REARRANGEMENT; RING-CLOSING METATHESIS REACTIONS; TANDEM PROCESS; TRICHLOROACETIMIDATES;

EID: 77954628306     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c004695g     Document Type: Article
Times cited : (36)

References (56)
  • 26
    • 77957982461 scopus 로고    scopus 로고
    • L. E. Overman, Wiley: Hoboken, NJ, 1-107 and references therein
    • L. E. Overman and N. E. Carpenter, In Organic Reactions, Ed., L. E. Overman,, Wiley: Hoboken, NJ, 2005; Vol. 66, 1-107 and references therein
    • (2005) Organic Reactions, Ed.
    • Overman, L.E.1    Carpenter In, N.E.2
  • 38
    • 33845377311 scopus 로고
    • The Masamune-Roush conditions for the HWE step were used. For reference see:
    • R. E. Ireland D. W. Norbeck J. Org. Chem. 1985 50 2198
    • (1985) J. Org. Chem. , vol.50 , pp. 2198
    • Ireland, R.E.1    Norbeck, D.W.2
  • 44
    • 0001855961 scopus 로고    scopus 로고
    • The relative stereochemistry of bicyclic lactam 4 was determined using NOE experiments. As reported by the groups of Itoh (reference 9b) and Snapper (reference 11b), the stereochemical outcome of the Kharasch cyclization supports an atom transfer radical mechanism
    • P. Schwab R. H. Grubbs J. W. Ziller J. Am. Chem. Soc. 1996 118 100
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 100
    • Schwab, P.1    Grubbs, R.H.2    Ziller, J.W.3
  • 45
    • 0003579939 scopus 로고
    • John Wiley and Sons: Chichester, Similar problems have been observed with other allylic trichloracetimidates containing side chains with coordinating groups and terminal alkenes. For example, see reference 8a
    • L. A. Paquette, Ed. Encyclopaedia of Reagents for Organic Synthesis, John Wiley and Sons: Chichester, 1995
    • (1995) Encyclopaedia of Reagents for Organic Synthesis
    • Paquette, Ed.L.A.1
  • 53
    • 74949098369 scopus 로고    scopus 로고
    • The enantiomeric excess of compounds 14, 15 and 16 was determined by chiral HPLC. See, experimental for full details The longer reaction times required for the rearrangement of allylic trichloroacetimidates 2 and 5 using the COP-Cl catalysts likely accounts for the lower yields for these series of compounds compared to the racemic analogues generated using bis(acetonitrile) palladium(ii) chloride in Table 1
    • A. Rodrigues E. E. Lee R. A. Batey Org. Lett. 2010 12 260
    • (2010) Org. Lett. , vol.12 , pp. 260
    • Rodrigues, A.1    Lee, E.E.2    Batey, R.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.