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Volumn 9, Issue 25, 2007, Pages 5239-5242

A tandem aza-claisen rearrangement and ring closing metathesis reaction for the synthesis of cyclic allylic trichloroacetamides

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EID: 37249079622     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702299c     Document Type: Article
Times cited : (39)

References (43)
  • 1
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    • For general reviews, see: a
    • For general reviews, see: (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
    • (1996) Chem. Rev , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 17
    • 33646064214 scopus 로고    scopus 로고
    • Overman, L. E, Ed, Wiley: Hoboken, NJ, and references therein
    • Overman, L. E.; Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: Hoboken, NJ, 2005; Vol. 66, pp 1-107 and references therein.
    • (2005) Organic Reactions , vol.66 , pp. 1-107
    • Overman, L.E.1    Carpenter, N.E.2
  • 31
    • 0000476716 scopus 로고    scopus 로고
    • For high yielding preparation of (E)-alkenes from the one-pot Swern oxidation and HWE reaction, we use Masamune-Roush conditions for the HWE step. For reference, see: Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masumune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
    • For high yielding preparation of (E)-alkenes from the one-pot Swern oxidation and HWE reaction, we use Masamune-Roush conditions for the HWE step. For reference, see: Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masumune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
  • 36
    • 37249085880 scopus 로고    scopus 로고
    • Allylic trichloroacetimidates are relatively unstable and, therefore, are not subjected to extensive purification. Hence, yields quoted for the preparation of the cyclic allylic trichloroacetamides are from the corresponding allylic alcohols
    • Allylic trichloroacetimidates are relatively unstable and, therefore, are not subjected to extensive purification. Hence, yields quoted for the preparation of the cyclic allylic trichloroacetamides are from the corresponding allylic alcohols.
  • 37
    • 37249086406 scopus 로고    scopus 로고
    • As highlighted in Scheme 3, use of Grubbs second-generation and Hoveyda-Grubbs second-generation catalysts gave cyclic allylic trichloroacetamide 6 in slightly higher yield than with the Grubbs first-generation catalyst. Nevertheless, in developing the subsequent reactions, we have used mainly Grubbs first-generation catalyst due to its relatively low cost and availability compared to the other catalysts.
    • As highlighted in Scheme 3, use of Grubbs second-generation and Hoveyda-Grubbs second-generation catalysts gave cyclic allylic trichloroacetamide 6 in slightly higher yield than with the Grubbs first-generation catalyst. Nevertheless, in developing the subsequent reactions, we have used mainly Grubbs first-generation catalyst due to its relatively low cost and availability compared to the other catalysts.
  • 43
    • 37249043448 scopus 로고    scopus 로고
    • The enantiomeric excess of compounds 14 and 15 was determined by chiral HPLC See Supporting Information for full details.
    • The enantiomeric excess of compounds 14 and 15 was determined by chiral HPLC See Supporting Information for full details.


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