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Volumn 692, Issue 26, 2007, Pages 5795-5798

Catalysis in water: Synthesis of β-amino amides by Sc(III) promoted condensation of silylketene pyridylthioacetal and imines

Author keywords

Catalysis; Reaction in water; Scandium triflate; Synthetic method

Indexed keywords

CATALYSIS; CONDENSATION; DERIVATIVES; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 36248967668     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.10.013     Document Type: Short Survey
Times cited : (7)

References (34)
  • 2
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    • Grieco P.A. (Ed), Blackie Academic & Professional, London
    • In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic & Professional, London
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  • 6
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    • For a very interesting discussion of enantioselective organocatalysis "in water" or "in the presence of water", see:
    • For a very interesting discussion of enantioselective organocatalysis "in water" or "in the presence of water", see:. Brogan A.P., Dickerson T.J., and Janda K.D. Angew. Chem., Int. Ed. 45 (2006) 8100
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 8100
    • Brogan, A.P.1    Dickerson, T.J.2    Janda, K.D.3
  • 10
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    • For the synthesis of these silylketene 2-pyridylthioacetals and their use in a non-catalytic synthesis of β-lactams, see:
    • For the synthesis of these silylketene 2-pyridylthioacetals and their use in a non-catalytic synthesis of β-lactams, see:. Annunziata R., Cinquini M., Cozzi F., Molteni V., and Schupp O. Tetrahedron 52 (1996) 2573
    • (1996) Tetrahedron , vol.52 , pp. 2573
    • Annunziata, R.1    Cinquini, M.2    Cozzi, F.3    Molteni, V.4    Schupp, O.5
  • 12
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    • The one-pot formation of the azetidinone ring takes advantage of the excellent leaving group nature of the 2-pyridylthio residue.
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    • Reviews: and references cited therein
    • Reviews:. Kobayashi S. Synlett (1994) 689 and references cited therein
    • (1994) Synlett , pp. 689
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    • and references cited therein
    • Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069 and references cited therein
    • (1999) Chem. Rev. , vol.99 , pp. 1069
    • Kobayashi, S.1    Ishitani, H.2
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    • note
    • cis = ca. 5.0-6.0 Hz).
  • 16
    • 36248934748 scopus 로고    scopus 로고
    • For a solvent-free, one-pot synthesis of β-lactams, see:
    • For a solvent-free, one-pot synthesis of β-lactams, see:. Puglisi A., Benaglia M., and Cozzi F. Eur. J. Org. Chem. (2007) 2865
    • (2007) Eur. J. Org. Chem. , pp. 2865
    • Puglisi, A.1    Benaglia, M.2    Cozzi, F.3
  • 17
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    • note
    • 4, filtered and concentrated. The resulting oil was then charged on top of a column and purified by flash chromatography with a 8:2 hexane:AcOEt mixture followed by 7:3 hexane:AcOEt mixture as eluant.
  • 18
    • 36248952195 scopus 로고    scopus 로고
    • note
    • 5: C, 65.27; H, 6.78; N, 7.25. Found: C, 65.31; H, 6.76; N, 7.23%.
  • 19
    • 36248940791 scopus 로고    scopus 로고
    • note
    • The reaction afforded always product 4 with the same diastereisomeric ratio (65/35) that was shown to be independent from the experimental conditions employed.
  • 21
    • 27144524535 scopus 로고    scopus 로고
    • For recent examples of reactions catalysed by ScTDS, see:
    • For recent examples of reactions catalysed by ScTDS, see:. Azoulay S., Manabe K., and Kobayashi S. Org. Lett. 7 (2005) 4593
    • (2005) Org. Lett. , vol.7 , pp. 4593
    • Azoulay, S.1    Manabe, K.2    Kobayashi, S.3
  • 23
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    • note
    • The use of 1 or 2 mol/eq of free 4-methoxy aniline in the condensation between silyl ketene acetal 1 (2 mol/eq) and imine 2 (1 mol/eq) did not improve the reaction yield and did not alter the diastereoisomeric ratio of product 4.
  • 24
    • 36249008595 scopus 로고    scopus 로고
    • note
    • 3: C, 73.82; H, 6.71; N, 7.17. Found: C, 73.79; H, 6.72; N, 7.19%.
  • 25
    • 36248987293 scopus 로고    scopus 로고
    • note
    • The reaction afforded always product 9 with the same diastereisomeric ratio (70/30) that was shown to be independent from the experimental conditions employed.
  • 26
    • 0034596298 scopus 로고    scopus 로고
    • Recovery and recycling of scandium tris(dodecyl sulfate) have not been clearly accomplished:
    • Recovery and recycling of scandium tris(dodecyl sulfate) have not been clearly accomplished:. Manabe K., Mori Y., Wakabayashi T., Nagayama S., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 7202
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7202
    • Manabe, K.1    Mori, Y.2    Wakabayashi, T.3    Nagayama, S.4    Kobayashi, S.5
  • 27
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    • For an example of recycle of supported scandium catalyst, see:
    • For an example of recycle of supported scandium catalyst, see:. Nagayama S., and Kobayashi S. Angew. Chem., Int. Ed. 39 (2000) 567
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 567
    • Nagayama, S.1    Kobayashi, S.2
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    • note
    • 2O, DCM, AcOEt, or hexanes/AcOEt mixtures.
  • 30
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    • For examples of organocatalysed reactions carried out under the continuous flow mode, see:
    • For examples of organocatalysed reactions carried out under the continuous flow mode, see:. Ishiara K., Hasegawa A., and Yamamoto H. Synlett (2002) 1296
    • (2002) Synlett , pp. 1296
    • Ishiara, K.1    Hasegawa, A.2    Yamamoto, H.3
  • 32
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    • note
    • Procedure for catalyst recycling: SKTA 1 was reacted with imine 7 as described in note [10]. After 48 h 0.085 g of SKTA 1 and 0.124 g of imine 7 were added to the aqueous phase and a second reaction allowed to proceed for 48 h. After three further iterations of this procedure (for a total five reaction cycles) amide 9 was isolated after silica gel chromatography in 31% yield along with 10% β-lactams 8c and 8t as described above.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.