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Volumn 128, Issue 40, 2006, Pages 13151-13160

Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: Competing routes to C-C bond formation

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; KETONES; PROBABILITY DENSITY FUNCTION; SUBSTRATES;

EID: 84962467066     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063201x     Document Type: Article
Times cited : (402)

References (77)
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    • (b) Special issue on organocatalysis; Houk, K. N., List, B., Eds. Acc. Chem. Res. 2004, 37, 487-631,
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    • For developments and applications of cyclohexylamine-derived bifunctional thiourea catalysts, see: (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672-12673.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672-12673
    • Okino, T.1    Hoashi, Y.2    Takemoto, Y.3
  • 24
    • 26844450640 scopus 로고    scopus 로고
    • For developments and applications of cinchona-derived bifunctional thiourea catalysts, see: (a) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367-6370.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6367-6370
    • McCooey, S.H.1    Connon, S.J.2
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    • For the first computations on thiourea-catalyzed reactions, see: (a) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217-220.
    • (2002) Org. Lett. , vol.4 , pp. 217-220
    • Schreiner, P.R.1    Wittkopp, A.2
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    • note
    • N⋯H values may partially arise from the fact that the positions of the H atoms in the X-ray measurements are not determined as such, but they are rather estimated by a fitting procedure using a simple model.
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    • The keto-enol tautomeric equilibrium of acetylacetone is known to be shifted toward the enolic form due to internal hydrogen bonding; see, for example: Moriyasu, M.; Kato, A.; Hashimoto, Y. J. Chem. Soc., Perkin Trans. 2 1986, 515-520.
    • (1986) J. Chem. Soc., Perkin Trans. 2 , pp. 515-520
    • Moriyasu, M.1    Kato, A.2    Hashimoto, Y.3
  • 65
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    • note
    • Several other coordination modes have been located as local minima for both binary complexes, which are reported in the Supporting Information.
  • 67
    • 0000234063 scopus 로고    scopus 로고
    • For reactions catalyzed by quaternary ammonium salts of cinchona alkaloids, see: (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12414-12415
    • Corey, E.J.1    Xu, F.2    Noe, M.C.3
  • 73
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    • note
    • For comparison, energy barriers estimated for the C-C bond formation step in proline-catalyzed intermolecular aldol reactions range between 9 and 15 kcal/mol: see ref 9e,f.
  • 75
    • 84962425910 scopus 로고    scopus 로고
    • note
    • 1-7) = 2.7 kcal/mol and RT = 0.59 kcal/mol).
  • 76
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    • note
    • For the full-energy diagram obtained with the solvated model, see the Supporting Information.
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    • note
    • Identification of the stationary points associated with the protonation process and the C-C bond formation is in progress.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.