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Volumn 56, Issue 24, 2000, Pages 3901-3907

The lithium amide induced rearrangement of epoxysulfones derived from bicyclo[2.2.1]heptane system

Author keywords

Bicyclic aliphatic compounds; Carbenes and carbenoids; Epoxides; Lithium amides

Indexed keywords

AMIDE; EPOXIDE; LITHIUM DERIVATIVE; NORBORNANE DERIVATIVE; SULFONE DERIVATIVE;

EID: 0034625356     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00294-5     Document Type: Article
Times cited : (9)

References (50)
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    • 2, -78°C, 70%) to give nortricyclanone derivative 21 (Aceña, J. L. PhD Thesis, 1996, Universidad Complutense de Madrid. Unpublished results). For related processes, see: (a)
    • 2, -78°C, 70%) to give nortricyclanone derivative 21 (Aceña, J. L. PhD Thesis, 1996, Universidad Complutense de Madrid. Unpublished results). For related processes, see: (a) Rajapaksa, D.; Keay, B. A.; Rodrigo, R. Can. J. Chem. 1984, 62, 826-827.
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    • note
    • 3CN as solvent and further elimination of one of the phenylsulfonyl groups employing t-BuOK in equimolecular amount lead to 2b in high yields (Scheme 10).
  • 36
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    • (b) For an enantioselective version of this process, see
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    • note
    • In comparative experiments with those reported by Crandall et al. (see Ref. 8a) and McDonald et al. (see Ref. 12a), we have observed that the unsubstituted bicyclo[2.2.1]hept-2-ene-exo-oxide reacts with LDA in the same conditions used in this work to give nortricyclanol 3a in 88% yield. These conditions should be compared with those reported (reflux, ether-benzene, 50 h).
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    • (b) We thank one of the referees for this observation
    • (b) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. We thank one of the referees for this observation.
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