메뉴 건너뛰기




Volumn 10, Issue 6, 2008, Pages 1271-1274

An efficient and straightforward access to sulfur substituted [2.2]paracyclophanes: Application to stereoselective sulfenate salt alkylation

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; SULFUR;

EID: 45549097591     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800161m     Document Type: Article
Times cited : (30)

References (47)
  • 1
    • 3242887372 scopus 로고    scopus 로고
    • Gleiter, R, Hopf, H, Eds; Wiley-VCH: Weinheim
    • (a) Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds; Wiley-VCH: Weinheim, 2004.
    • (2004) Modern Cyclophane Chemistry
  • 13
    • 5144227167 scopus 로고    scopus 로고
    • Sulfonamides: Braddock, D., C.; MacGilp, I. D.; Perry, B. G. Adv. Synth. Catal. 2004, 346, 1117-1130.
    • Sulfonamides: Braddock, D., C.; MacGilp, I. D.; Perry, B. G. Adv. Synth. Catal. 2004, 346, 1117-1130.
  • 14
    • 58149147988 scopus 로고    scopus 로고
    • Sulfonic acid
    • Sulfonic acid:
  • 17
    • 58149151898 scopus 로고    scopus 로고
    • The sulfur atom was introduced via a Newman-Kwart reaction, treatment of lithiated species with elemental sulfur or a Pd-catalysis with triisopropylsilanethiol. See ref 2
    • The sulfur atom was introduced via a Newman-Kwart reaction, treatment of lithiated species with elemental sulfur or a Pd-catalysis with triisopropylsilanethiol. See ref 2.
  • 18
    • 58149150454 scopus 로고    scopus 로고
    • To the best of our knowledge, only the t-butylsulfanyl derivative of 3 (alkyl, t-Bu) has been described so far. See ref 4a
    • To the best of our knowledge, only the t-butylsulfanyl derivative of 3 (alkyl = t-Bu) has been described so far. See ref 4a.
  • 21
    • 58149172599 scopus 로고    scopus 로고
    • It was previously shown that the aromatic sulfonation of 1 with sulfur trioxide, in the presence of 1, 4-dioxane, proceeds cleanly to afford [2.2]paracyclophane-4-sulfonic acid. See ref 6
    • It was previously shown that the aromatic sulfonation of 1 with sulfur trioxide, in the presence of 1, 4-dioxane, proceeds cleanly to afford [2.2]paracyclophane-4-sulfonic acid. See ref 6.
  • 33
    • 58149155358 scopus 로고    scopus 로고
    • Excellent diastereocontrols were already reported using isoborneol, cysteine and (a)-phenylethylamine derivatives. See ref 13
    • Excellent diastereocontrols were already reported using isoborneol, cysteine and (a)-phenylethylamine derivatives. See ref 13.
  • 34
    • 58149150452 scopus 로고    scopus 로고
    • This compound was prepared in a 93% overall yield by Michael addition of 3-sulfanylpropanoic acid methyl ester on methyl acrylate, followed by oxidation with NaIC4. See Supporting Information
    • 4. See Supporting Information.
  • 35
    • 0346970844 scopus 로고    scopus 로고
    • 2/2, 2, 2-trifluoroethanol combination was used: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29.
    • 2/2, 2, 2-trifluoroethanol combination was used: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29.
  • 36
    • 58149160631 scopus 로고    scopus 로고
    • Previously reported [2.2]paracyclophan-4-yl sulfoxides were synthetized using oxidation or Andersen approaches. See ref 4
    • Previously reported [2.2]paracyclophan-4-yl sulfoxides were synthetized using oxidation or Andersen approaches. See ref 4.
  • 37
    • 58149162392 scopus 로고    scopus 로고
    • Crystal structures of 9 showed that the S-O bond is almost in the same plane than the arene, the oxygen atom oriented towards the ortho proton (torsional angle values between S-O and C4-C5 ranging from -8.84 to 1.8°). See Supporting Information.
    • Crystal structures of 9 showed that the S-O bond is almost in the same plane than the arene, the oxygen atom oriented towards the ortho proton (torsional angle values between S-O and C4-C5 ranging from -8.84 to 1.8°). See Supporting Information.
  • 39
    • 58149151899 scopus 로고    scopus 로고
    • 6 was prepared in an 78% overall yield by a regioselective radical addition of thiol 2 on vinyltrimethylsilane in the presence of a catalytic amount of AIBN (1%), followed by oxidation
    • Sulfoxide 6 was prepared in an 78% overall yield by a regioselective radical addition of thiol 2 on vinyltrimethylsilane in the presence of a catalytic amount of AIBN (1%), followed by oxidation. See Supporting Information.
    • See Supporting Information
    • Sulfoxide1
  • 40
    • 58149143669 scopus 로고    scopus 로고
    • Previously reported conformational studies involving calculations concern exclusively ethenesulfenate species. See ref 13
    • Previously reported conformational studies involving calculations concern exclusively ethenesulfenate species. See ref 13.
  • 44
    • 58149162391 scopus 로고    scopus 로고
    • A remarkable difference in chemical shift, resulting of the strong anisotropy of the sulfinyl group, is observed for the signal of one diastereotopic H2. It occurs in the range of 2.6-2.9 ppm in 9 but is substantially deshielded at & = 4.1-4.2 ppm in 10. See also ref 4a.
    • A remarkable difference in chemical shift, resulting of the strong anisotropy of the sulfinyl group, is observed for the signal of one diastereotopic H2. It occurs in the range of 2.6-2.9 ppm in 9 but is substantially deshielded at & = 4.1-4.2 ppm in 10. See also ref 4a.
  • 45
    • 58149151897 scopus 로고    scopus 로고
    • 6-arene)chromium(O) complexes:
    • 6-arene)chromium(O) complexes:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.