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Volumn 47, Issue 41, 2008, Pages 7872-7875

A highly reactive and enantioselective bifunctional organocatalyst for the methanolytic desymmetrization of cyclic anhydrides: Prevention of catalyst aggregation

Author keywords

Asymmetric catalysis; Bifunctional catalysts; Densityfunctional calculations; Desymmetrization; Organocatalysis

Indexed keywords


EID: 54749152753     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801636     Document Type: Article
Times cited : (152)

References (39)
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    • It was reported that hydroquinine-based thioureas are thermally unstable: B. Vakulya, S. Varga, A. Csámpai, T. Soós, Org. Lett. 2005, 7, 1967-1969.
    • It was reported that hydroquinine-based thioureas are thermally unstable: B. Vakulya, S. Varga, A. Csámpai, T. Soós, Org. Lett. 2005, 7, 1967-1969.
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    • For the preparation and characterization of I, see the Supporting Information.
    • For the preparation and characterization of I, see the Supporting Information.
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    • It was generally accepted that the nucleophile can be activated through deprotonation by the quinuclidine base: H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417-430.
    • It was generally accepted that the nucleophile can be activated through deprotonation by the quinuclidine base: H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417-430.
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    • However, recent computational results showed that the tertiary amine moiety of the catalyst does not act to deprotonate the nucleophile in the enantioselective Michael addition of acetyl-acetone to a nitroolefin in the presence of a thiourea-based chiral organocatalyst: A. Hamza, G. Schubert, T. Soós, I. Pápai, J. Am. Chem. Soc. 2006, 128, 13151-13160.
    • However, recent computational results showed that the tertiary amine moiety of the catalyst does not act to deprotonate the nucleophile in the enantioselective Michael addition of acetyl-acetone to a nitroolefin in the presence of a thiourea-based chiral organocatalyst: A. Hamza, G. Schubert, T. Soós, I. Pápai, J. Am. Chem. Soc. 2006, 128, 13151-13160.
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    • [13d,e] have already proven to be efficient chiral organocatalysts for a variety of interesting organic reactions. Their excellent catalytic efficiency has been attributed in part to the strongly hydrogen bond donating sulfonamide moiety; for selected examples, see: a W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393-1395;
    • [13d,e] have already proven to be efficient chiral organocatalysts for a variety of interesting organic reactions. Their excellent catalytic efficiency has been attributed in part to the strongly hydrogen bond donating sulfonamide moiety; for selected examples, see: a) W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393-1395;
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    • All calculations were performed with Spartan '04 Windows (Wavefunction). Preliminary global minimum-energy structures were obtained by molecular-mechanics computation and further refined by DFT computation (B3LYP at the 6-31G* level).
    • All calculations were performed with Spartan '04 Windows (Wavefunction). Preliminary global minimum-energy structures were obtained by molecular-mechanics computation and further refined by DFT computation (B3LYP at the 6-31G* level).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.