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Volumn 73, Issue 21, 2008, Pages 8469-8473

Dicobalt hexacarbonyl complexes of alkynyl imines in a sequential Staudinger/Pauson-Khand process. A route to new fused tricyclic β-lactams

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

EID: 55249088970     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801668b     Document Type: Article
Times cited : (25)

References (79)
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    • 1H NMR of the crude mixture. The intermediate imines are likely to be unstable.
    • 1H NMR of the crude mixture. The intermediate imines are likely to be unstable.
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    • and references therein. For a discussion of the mechanism, see
    • For a discussion of the mechanism, see: Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6060-6069, and references therein.
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    • Shibata, T.1
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    • For previous synthesis of bicyclic amino esters via Pauson-Khand reaction, see: a
    • For previous synthesis of bicyclic amino esters via Pauson-Khand reaction, see: (a) Bolton, G. L.; Hodges, J. C.; Rubin, J. R. Tetrahedron 1997, 53, 6611-6634.
    • (1997) Tetrahedron , vol.53 , pp. 6611-6634
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    • For related examples of diastereocontrol with a substituent in position α relative to the triple bond, see: (a) Exon, C, Magnus, P. J. Am. Chem. Soc. 1983, 105, 2477-2478
    • For related examples of diastereocontrol with a substituent in position α relative to the triple bond, see: (a) Exon, C.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 2477-2478.
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    • Steric hindrance is responsible for the low yield in this particular case; see ref 4a and Mukai, C, Uchiyama, U, Sakamoto, S, Hanaoka, M. Tetrahedron Lett. 1995, 36, 5761-5764
    • Steric hindrance is responsible for the low yield in this particular case; see ref 4a and Mukai, C.; Uchiyama, U.; Sakamoto, S.; Hanaoka, M. Tetrahedron Lett. 1995, 36, 5761-5764.
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    • Very similar selectivity and yields were obtained from the p-MeOPh (PMP) derivative.
    • Very similar selectivity and yields were obtained from the p-MeOPh (PMP) derivative.
  • 79
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    • The diastereoselectivity, likely to be the same as in the case of six-membered ring closure, could not be ascertained
    • The diastereoselectivity, likely to be the same as in the case of six-membered ring closure, could not be ascertained.


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