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Volumn 137, Issue 5, 2015, Pages 2116-2127

Origins of stereoselectivity in intramolecular aldol reactions catalyzed by cinchona amines

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONDENSATION REACTIONS; DISPERSIONS; HYDROGEN; HYDROGEN BONDS; KETONES; STEREOSELECTIVITY;

EID: 84922770554     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja513096x     Document Type: Article
Times cited : (71)

References (145)
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    • For a recent review of asymmetric organocatalytic methods to access chiral cyclohexenone skeletons, see
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    • Yang, X.1    Wang, J.2    Li, P.3
  • 34
    • 84882396941 scopus 로고    scopus 로고
    • Cinchona Alkaloids
    • Zhou, Q.-L. Wiley-VCH: Weinheim, Germany
    • Li, H.; Chen, Y.; Deng, L. Cinchona Alkaloids. In Privileged Chiral Ligands and Catalysts; Zhou, Q.-L., Ed.; Wiley-VCH: Weinheim, Germany, 2011; pp 361-408.
    • (2011) Privileged Chiral Ligands and Catalysts , pp. 361-408
    • Li, H.1    Chen, Y.2    Deng, L.3
  • 62
    • 77953493911 scopus 로고    scopus 로고
    • Ed. Springer: Dordrecht, The Netherlands
    • Aldol Reactions; Mahrwald, R., Ed.; Springer: Dordrecht, The Netherlands, 2009.
    • (2009) Aldol Reactions
    • Mahrwald, R.1
  • 95
    • 84912096260 scopus 로고    scopus 로고
    • Weak Intermolecular Interactions: A Supermolecular Approach
    • Leszczynski, J. Springer: Dordrecht, The Netherlands
    • Waller, M.; Grimme, S. Weak Intermolecular Interactions: A Supermolecular Approach. In Handbook of Computational Chemistry; Leszczynski, J., Ed.; Springer: Dordrecht, The Netherlands, 2012; pp 443-466.
    • (2012) Handbook of Computational Chemistry , pp. 443-466
    • Waller, M.1    Grimme, S.2
  • 98
    • 84898490480 scopus 로고    scopus 로고
    • For a recent large-scale evaluation of several quantum-chemical methods in the calculation of noncovalent interactions, including a timing analysis of different density functionals, see: Li, A.; Muddana, H. S.; Gilson, M. K. J. Chem. Theory Comput. 2014, 10, 1563-1575
    • (2014) J. Chem. Theory Comput. , vol.10 , pp. 1563-1575
    • Li, A.1    Muddana, H.S.2    Gilson, M.K.3
  • 111
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    • MacroModel, version 9.9; Schrödinger, LLC: New York
    • MacroModel, version 9.9; Schrödinger, LLC: New York, 2012.
    • (2012)
  • 114
    • 84922831588 scopus 로고    scopus 로고
    • Cinchonine
    • Royal Society of Chemistry: Cambridge, U.K. (accessed June 16)
    • Cinchonine. In The Merck Index Online; Royal Society of Chemistry: Cambridge, U.K.; https://www.rsc.org/Merck-Index/monograph/mono1500002290 (accessed June 16, 2014).
    • (2014) The Merck Index Online
  • 128
    • 84889779443 scopus 로고    scopus 로고
    • In most cases, the vinyl group on the quinuclidine ring has little influence over the sense of asymmetric induction in reactions organocatalyzed by cinchona alkaloid derivatives. For a rare example in which the identity of this ring substituent dramatically affects the product outcome in an organocatalyzed reaction, see: Qian, H.; Yu, X.; Zhang, J.; Sun, J. J. Am. Chem. Soc. 2013, 135, 18020-18023
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 18020-18023
    • Qian, H.1    Yu, X.2    Zhang, J.3    Sun, J.4
  • 142
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    • The importance of dispersion effects in stereocontrol in organocatalytic reactions has also been described by Uyeda and Jacobsen, who found that the stereoselectivities computed using the dispersion-inclusive M05-2X functional for a guanidinium-catalyzed enantioselective Claisen rearrangement correlate better with experiment than those computed using B3LYP. See: Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 5062-5075
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 5062-5075
    • Uyeda, C.1    Jacobsen, E.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.