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Volumn 64, Issue 18, 2008, Pages 3943-3952

Intramolecular conjugate addition of γ- and δ-trichloroacetimidoyloxy-α,β-unsaturated esters in an acyclic system

Author keywords

Intramolecular conjugate addition; Trichloroacetimidate; Vancosamine

Indexed keywords

ALCOHOL; AMINE; DEXTRO VANCOSAMINE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

EID: 40849126443     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.061     Document Type: Article
Times cited : (16)

References (42)
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  • 10
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    • A few examples of intramolecular conjugate additions of trichloroacetimidates, which were prepared in situ, in a cyclic system were reported:
    • A few examples of intramolecular conjugate additions of trichloroacetimidates, which were prepared in situ, in a cyclic system were reported:
  • 13
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    • For α,β-unsaturated sulfones, see:
    • For α,β-unsaturated sulfones, see:. Li X.C., and Fuchs P.L. Synlett (1994) 629-630
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  • 14
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    • There are some useful reactions involving the trichloroacetimidates for the introduction of a nitrogen functionality.
    • There are some useful reactions involving the trichloroacetimidates for the introduction of a nitrogen functionality.
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    • For electrophile-promoted intramolecular aminations of trichloroacetimidates derived from allylic and homoallylic alcohols, see: and references therein
    • For electrophile-promoted intramolecular aminations of trichloroacetimidates derived from allylic and homoallylic alcohols, see:. Lee H.-S., and Kang S.H. Synlett (2004) 1673-1685 and references therein
    • (2004) Synlett , pp. 1673-1685
    • Lee, H.-S.1    Kang, S.H.2
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    • For acid-promoted intramolecular epoxide opening of trichloroacetimidates, see:
    • For acid-promoted intramolecular epoxide opening of trichloroacetimidates, see:. Bernet B., and Vasella A. Tetrahedron Lett. 24 (1983) 5491-5494
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5491-5494
    • Bernet, B.1    Vasella, A.2
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    • For Overman rearrangement, see:
    • For Overman rearrangement, see:. Overman L.E. Acc. Chem. Res. 13 (1980) 218-224
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    • Overman, L.E.1
  • 22
    • 40849138214 scopus 로고    scopus 로고
    • Starting allylic alcohols were, respectively, prepared according to the literatures below:
    • Starting allylic alcohols were, respectively, prepared according to the literatures below:
  • 24
    • 40849098937 scopus 로고    scopus 로고
    • lit. 5;
    • lit. 5;
  • 25
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    • lit. 6;
    • lit. 6;
  • 28
    • 40849100620 scopus 로고    scopus 로고
    • note
    • During the imidate formation a trace amount of conjugate adducts was obtained at low temperature and prolonged time or increased temperature afforded the products, but only in low yield.
  • 29
    • 0001345433 scopus 로고
    • It was reported that in an oxazoline ring the small coupling constant (ca. 6 Hz) corresponded to trans form and the large one (ca. 9 Hz) to cis form; see:
    • It was reported that in an oxazoline ring the small coupling constant (ca. 6 Hz) corresponded to trans form and the large one (ca. 9 Hz) to cis form; see:. Roush W.R., Straub J.A., and Brown R.J. J. Org. Chem. 52 (1987) 5127-5136
    • (1987) J. Org. Chem. , vol.52 , pp. 5127-5136
    • Roush, W.R.1    Straub, J.A.2    Brown, R.J.3
  • 31
    • 40849127152 scopus 로고    scopus 로고
    • Starting homoallylic alcohols were, respectively, prepared according to the literatures below:
    • Starting homoallylic alcohols were, respectively, prepared according to the literatures below:
  • 34
    • 40849116718 scopus 로고    scopus 로고
    • lit. 5;
    • lit. 5;
  • 36
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    • note
    • H-5′ax,H-6′=ca. 11 Hz) of 5a.
  • 37
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    • Syntheses of vancosamine derivatives, see:
    • Syntheses of vancosamine derivatives, see:. Hsu D.-S., Matsumoto T., and Suzuki K. Synlett (2006) 469-471
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    • Hsu, D.-S.1    Matsumoto, T.2    Suzuki, K.3
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    • The known acetonide 7 was prepared from l-threonine, see: and references therein
    • The known acetonide 7 was prepared from l-threonine, see:. Aoyagi S., Wang T.-C., and Kibayashi C. J. Am. Chem. Soc. 115 (1993) 11393-11409 and references therein
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11393-11409
    • Aoyagi, S.1    Wang, T.-C.2    Kibayashi, C.3
  • 40
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    • note
    • The irradiation of methyne hydrogen (H-5′) on the cis-oxazoline 10 yielded no NOE on the methylene protons (H-2). On the contrary, the irradiation of the hydrogen corresponding to the trans-oxazoline 11 yielded an NOE of ca. 4% on the one methylene proton (H-2).
  • 42


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.