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Volumn 12, Issue 23, 2010, Pages 5494-5497

Tandem nucleophilic addition-intramolecular aza-michael reaction: Facile synthesis of chiral fluorinated isoindolines

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; INDOLINE; ISOINDOLE DERIVATIVE;

EID: 78650352857     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102341n     Document Type: Article
Times cited : (74)

References (40)
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    • The reaction was also performed with the (S)- N -(p -tolylsulfinyl)imine derivative; however, no product was formed, and mostly starting material was recovered from the reaction mixture
    • The reaction was also performed with the (S)- N -(p -tolylsulfinyl)imine derivative; however, no product was formed, and mostly starting material was recovered from the reaction mixture.
  • 22
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    • For a recent and exhaustive review about tert -butanesulfinamide and its use in synthesis, see Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600
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    • 19F NMR on the crude NMR spectra. They were found inaltered after column chromatography. See
    • 19F NMR on the crude NMR spectra. They were found inaltered after column chromatography. See
  • 30
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    • In all cases, the intermediate product 3a - l could be isolated. Treatment of the former with t -BuOK in THF at -40 °C gave the corresponding cyclized product 2a - l
    • In all cases, the intermediate product 3a - l could be isolated. Treatment of the former with t -BuOK in THF at -40 °C gave the corresponding cyclized product 2a - l.
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    • The required substrates (R, S)- 1a - l are conveniently synthesized from commercially available starting materials in a two-step sequence (see Supporting Information)
    • The required substrates (R, S)- 1a - l are conveniently synthesized from commercially available starting materials in a two-step sequence (see Supporting Information).
  • 32
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    • Assuming the reversibility of the aza-Michael addition (see ref 6d) the formation of the thermodynamic product is expected. As can be inferred from the ORTEP diagram (Figure 1, right side), the substituents at the 1 and 3 positions are oriented anti to the bulky substituent on the nitrogen (thus syn to each other)
    • Assuming the reversibility of the aza-Michael addition (see ref 6d) the formation of the thermodynamic product is expected. As can be inferred from the ORTEP diagram (Figure 1, right side), the substituents at the 1 and 3 positions are oriented anti to the bulky substituent on the nitrogen (thus syn to each other).
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    • During the deprotection step, a transesterification reaction with MeOH was observed
    • During the deprotection step, a transesterification reaction with MeOH was observed.
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    • For the addition of 5 to N -(tert -butanesulfinyl)imines, see
    • For the addition of 5 to N -(tert -butanesulfinyl)imines, see: Li, Y.; Ni, C.; Liu, J.; Zhang, L.; Zheng, J.; Zhu, L.; Hu, J. Org. Lett. 2006, 8, 1693
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    • Li, Y.1    Ni, C.2    Liu, J.3    Zhang, L.4    Zheng, J.5    Zhu, L.6    Hu, J.7
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    • For the addition of 6 to N -(tert -butanesulfinyl)aldimines, see
    • For the addition of 6 to N -(tert -butanesulfinyl)aldimines, see: Li, Y.; Hu, J. Angew. Chem., Int. Ed. 2005, 44, 5882
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    • Li, Y.1    Hu, J.2
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    • For the addition of 6 to N -(tert -butanesulfinyl)ketimines, see
    • For the addition of 6 to N -(tert -butanesulfinyl)ketimines, see: Liu, J.; Hu, J. Chem. - Eur. J. 2010, 16, 11443
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    • Liu, J.1    Hu, J.2
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    • Moreover, 28% of the noncyclized precursor 3m was also obtained
    • Moreover, 28% of the noncyclized precursor 3m was also obtained.
  • 39
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    • Other methods described for desulfonylation, such as Mg/MeOH, Mg/DMF, and Raney Ni proved ineffective for these systems
    • Other methods described for desulfonylation, such as Mg/MeOH, Mg/DMF, and Raney Ni proved ineffective for these systems.
  • 40
    • 78650393015 scopus 로고    scopus 로고
    • In the desulfonylation step, a transesterification reaction with MeOH took place
    • In the desulfonylation step, a transesterification reaction with MeOH took place.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.