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Volumn 73, Issue 21, 2008, Pages 8643-8646

N-carbamate protected α-amidoalkyl-p-tolylsulfones: Convenient substrates in the aza-Morita-Baylis-Hillman reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMICAL BONDS; CHEMICAL REACTIONS; HYDROCARBONS; OLEFINS; ORGANIC COMPOUNDS; RATE CONSTANTS;

EID: 55249089670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801616d     Document Type: Article
Times cited : (18)

References (107)
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    • For reviews on the Morita-Baylis-Hillman reaction and its aza-counterpart, see: (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
    • (1996) Tetrahedron , vol.52 , pp. 8001
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  • 54
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    • For the use of N-phosphorylated and N-phosphinylated imines and their thio analogues, see: (a) Zwierzak, A.; Napieraj, A. Phosphorus, Sulfur and Silicon 1999, 144-146, 93.
    • For the use of N-phosphorylated and N-phosphinylated imines and their thio analogues, see: (a) Zwierzak, A.; Napieraj, A. Phosphorus, Sulfur and Silicon 1999, 144-146, 93.
  • 57
    • 55249096785 scopus 로고    scopus 로고
    • See ref 3p
    • (d) See ref 3p.
  • 58
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    • For the use of N-(aryl)imines, see: (a) Liu, X.; Chai, Z.; Zhao, G.; Zhu, S. J. Fluorine Chem. 2005, 126, 1215.
    • For the use of N-(aryl)imines, see: (a) Liu, X.; Chai, Z.; Zhao, G.; Zhu, S. J. Fluorine Chem. 2005, 126, 1215.
  • 60
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    • See ref 3r,s
    • (c) See ref 3r,s.
  • 75
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    • 4-mediated Baylis-Hillman reactions, see: (l) Li, G.; Wei, H.-X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1.
    • 4-mediated Baylis-Hillman reactions, see: (l) Li, G.; Wei, H.-X.; Gao, J. J.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1.
  • 76
    • 0037128471 scopus 로고    scopus 로고
    • For an alternative synthesis of N-Boc and N-Cbz protected aza-MBH-type adducts, see: (a) Ciclosi, M.; Fava, C.; Galeazzi, R.; Orena, M.; Sepulveda-Arques, J. Tetrahedron Lett. 2002, 43, 2199.
    • For an alternative synthesis of N-Boc and N-Cbz protected aza-MBH-type adducts, see: (a) Ciclosi, M.; Fava, C.; Galeazzi, R.; Orena, M.; Sepulveda-Arques, J. Tetrahedron Lett. 2002, 43, 2199.
  • 85
    • 55249091214 scopus 로고    scopus 로고
    • In our hands, attempted repetition of a three-component procedure elaborated by Bartenshaw and Kahn8a using tert-butyl or benzylcarbamate, benzaldehyde, methyl acrylate, and Ph3P 20 mol , as catalyst, resulted in the formation of the desired N-Boc or N-Cbz aza-adducts in less than 7% yield after 2 d at 40°C in 2-propanol, as confirmed by 1H NMR analysis of the crude reaction mixture
    • 1H NMR analysis of the crude reaction mixture.
  • 86
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    • For reviews, see: a
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    • (2005) Chem. Rev , vol.105 , pp. 3949
    • Petrini, M.1
  • 88
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    • For the synthesis of N-Boc and N-Cbz protected α-amidosulfones, see: (a) Engeberts, J. B. F. N.; Strating, J.Rec. Trav. Chim. Pays-Bas 1964, 83, 733.
    • For the synthesis of N-Boc and N-Cbz protected α-amidosulfones, see: (a) Engeberts, J. B. F. N.; Strating, J.Rec. Trav. Chim. Pays-Bas 1964, 83, 733.
  • 95
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    • For selected recent applications of α-amidosulfones, see: a
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    • (2005) Tetrahedron , vol.61 , pp. 8536
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    • A mixture of the corresponding (Z/E)-1-[(tert-butoxycarbonyl)amino]propenes (75:25 Z/E) was isolated in 72% yield from the reaction of N-Boc α-amidoalkyl-p-tolylsulfones 4, derived from propionaldehyde (R = Et), and methyl acrylate in the presence of DABCO (1.2 equiv) after 2 weeks at room temperature.
    • A mixture of the corresponding (Z/E)-1-[(tert-butoxycarbonyl)amino]propenes (75:25 Z/E) was isolated in 72% yield from the reaction of N-Boc α-amidoalkyl-p-tolylsulfones 4, derived from propionaldehyde (R = Et), and methyl acrylate in the presence of DABCO (1.2 equiv) after 2 weeks at room temperature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.