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Volumn 129, Issue 21, 2007, Pages 6756-6764

Chiral Brønsted acid catalyzed enantioselective Mannich-type reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; ENANTIOSELECTIVITY; ESTERS; GEOMETRY; REACTION KINETICS;

EID: 84962407641     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0684803     Document Type: Article
Times cited : (273)

References (120)
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    • Please see Scheme 4 in the Supporting Information for details.
    • Please see Scheme 4 in the Supporting Information for details.
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    • After our submission of the manuscript, a report on the mechanistic and computational study on the phosphoric acid catalysis has been published. See
    • After our submission of the manuscript, a report on the mechanistic and computational study on the phosphoric acid catalysis has been published. See: Gridnev, I. D.; Kouchi, M.; Sorimachi, K.; Terada, M. Tetrahedron Lett. 2007, 48, 497-500.
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    • In general, the DFT methods are not enough to correctly evaluate dispersion interaction in the weakly bounded system such as π-stacking interaction. It has been recently reported, however, that a half-and-half functional reproduces geometries and energetics for a π-stacked system with reasonable accuracy. See: a
    • In general, the DFT methods are not enough to correctly evaluate dispersion interaction in the weakly bounded system such as π-stacking interaction. It has been recently reported, however, that a half-and-half functional reproduces geometries and energetics for a π-stacked system with reasonable accuracy. See: (a) Waller, M. P.; Robertazzi, A.; Platts, J. A.; Hibbs, D. E.; Williams, P. A. J. Comput. Chem. 2006, 27, 491-504.
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    • The mesityl group (in 1c) has a different role from that of the 4-nitrophenyl group for the re-facial selectivity. It would generate a significant steric effect increasing the repulsive interaction for the SiMe 3 group of Nu. We are going to study other substituted BIPOL models
    • 3 group of Nu. We are going to study other substituted BIPOL models.


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