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Beilstein J. Org. Chem. 2013, 9, 155–165, doi:10.3762/bjoc.9.18
Graphical Abstract
Scheme 1: Activation of amine-bonded Michael acceptors by protonation versus Lewis acid interaction.
Scheme 2: Synthesis of 4-hydroxycoumarin derivatives by Michael addition [19-27].
Scheme 3: Precatalysts 5–8 and synthesis from chiral 1,2-diamines and 2-sulfobenzoic anhydrides.
Figure 1: X-ray crystallographic structure of 5. The conformation of the 2-sulfobenzoic moiety is fixed by hy...
Figure 2: Michael acceptors employed as substrates in the nucleophilic addition of 4-hydroxycoumarin (1).
Scheme 4: Computationally analyzed pathways A (C-protonation), and B (N-protonation), arising from the additi...
Scheme 5: Computed energy profile for reaction path A (C-protonation) and B (N-protonation) corresponding to ...
Figure 3: Enantio-determining transition states arising from the addition of 4-hydroxycoumarin to cyclohexeno...
Figure 4: The competing enantio-determining transition structures TS-14a and TS-14g. The reason for the desta...