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Volumn 13, Issue 12, 2011, Pages 3052-3055

Asymmetric synthesis of α-alkyl α-selenocarbonyl compounds catalyzed by bifunctional organocatalysts

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ESTER; KETONE; ORGANOSELENIUM DERIVATIVE; THIOUREA;

EID: 79958846486     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200923p     Document Type: Article
Times cited : (56)

References (48)
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    • In humans, 25 selenoproteins have been identified, many of which have unknown functions and remain to be explored. For leading references, see
    • In humans, 25 selenoproteins have been identified, many of which have unknown functions and remain to be explored. For leading references, see: Kryukov, G. V.; Castellano, S.; Novoselov, S. V.; Lobanov, A. V.; Zehtab, O.; Guingo, R.; Gladyshev, V. N. Science 2003, 300, 1439
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    • Despite their interest, only a very few methods concerning the organocatalytic synthesis of enantiomerically pure secondary seleno compounds have been reported. For example, see
    • Despite their interest, only a very few methods concerning the organocatalytic synthesis of enantiomerically pure secondary seleno compounds have been reported. For example, see: Winberg, H.; Pluim, H. Tetrahedron Lett. 1979, 1251
    • (1979) Tetrahedron Lett. , pp. 1251
    • Winberg, H.1    Pluim, H.2
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    • For a recent review about a bifunctional cinchona alkaloid based on thiourea catalysis, see:, For an account of multifunctional thioureas, see:; Bull. Chem. Soc. Jpn. 2008, 785 For selected recent examples of thiourea bifunctional catalysis, see:; Angew. Chem., Int. Ed. 2008, 47, 4177
    • For a recent review about a bifunctional cinchona alkaloid based on thiourea catalysis, see: Connon, S. J. Chem. Commun. 2008, 2499 For an account of multifunctional thioureas, see: Miyabe, H; Takemoto, Y. Bull. Chem. Soc. Jpn. 2008, 81, 785 For selected recent examples of thiourea bifunctional catalysis, see: Wang, J.; Xie, H.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177
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    • Chem. Commun. 2011, DOI: 10.1039/C1CC11124H
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    • 2 (see SI). The OH group at the quinine is presumably converted into O-Se-Ph (for an example in the reaction of PhSeCl with alcohols, see:;), whereas the thiourea evolves into a very complex mixture of species. It would explain the absence of catalytic activity and the formation of the racemic mixtures. Moreover, we have checked that this reaction occured in the absence of catalyst
    • 2 (see SI). The OH group at the quinine is presumably converted into O-Se-Ph (for an example in the reaction of PhSeCl with alcohols, see: Osajda, M.; Młochowski, J. Tetrahedron 2002, 58, 7531), whereas the thiourea evolves into a very complex mixture of species. It would explain the absence of catalytic activity and the formation of the racemic mixtures. Moreover, we have checked that this reaction occured in the absence of catalyst
    • (2002) Tetrahedron , vol.58 , pp. 7531
    • Osajda, M.1    Młochowski, J.2
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    • Several and different conditions of varying solvent, temperatures, and equivalence were tried. For more details, see SI
    • Several and different conditions of varying solvent, temperatures, and equivalence were tried. For more details, see SI.
  • 46
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    • Selenocyclohexanone and the opened derivatives (1,2-diphenyl-2- (phenylselanyl)ethanone and 1-1-phenyl-2-(phenylselanyl)propan-1-one) did not react under any of the catalytic conditions of Tables 2 and 3
    • α-Selenocyclohexanone and the opened derivatives (1,2-diphenyl-2-(phenylselanyl)ethanone and 1-1-phenyl-2-(phenylselanyl)propan- 1-one) did not react under any of the catalytic conditions of Tables 2 and 3.
  • 47
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    • CCDC 809359 (8a) contains the supplementary crystallographic data. These data can be obtained free of charge at [E-mail: deposit@ccdc.cam.ac.uk ]
    • CCDC 809359 (8a) contains the supplementary crystallographic data. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [E-mail: deposit@ccdc.cam.ac.uk ].
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    • For a computational study of the H-bond with Se compounds, see
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    • (2010) J. Mol. Struct. , vol.959 , pp. 1
    • Madzhidov, T.I.1    Chmutova, G.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.