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Beilstein J. Org. Chem. 2012, 8, 323–329, doi:10.3762/bjoc.8.35
Graphical Abstract
Scheme 1: Dioxane dibromide-mediated solvent-free bromination of substituted coumarins.
Scheme 2: Failure of DD to react with coumarins substituted with an electron-withdrawing group.
Scheme 3: Efficacy of the solvent-free bromination protocol with DD.
Figure 1: Mechanism for bromination of the heterocyclic ring.
Figure 2: Mechanism for bromination of the carbocyclic ring.
Beilstein J. Org. Chem. 2010, 6, 748–755, doi:10.3762/bjoc.6.94
Scheme 1: Facile reduction of γ-aryl-γ-ketoesters to the corresponding diols with methanolic NaBH4 at room te...
Scheme 2: Facile reduction of γ-aryl-α,β-unsaturated-γ-ketoesters to the diols with methanolic NaBH4 at room ...
Scheme 3: Facile reduction of γ-alkyl-γ-ketoester to the corresponding lactone with methanolic NaBH4 at room ...
Scheme 4: Reduction of methyl o-benzoylbenzoate with methanolic NaBH4.
Scheme 5: Reluctance of ester 8 towards reduction with methanolic NaBH4 at room temperature.
Scheme 6: Intermediacy of a lactone in the formation of diol.
Scheme 7: Diol formation from γ-aryl-α,β-unsaturated-γ-ketoester through the intermediacy of a saturated lact...
Figure 1: Mechanistic rationale for diol formation during the reduction of a γ-aryl-α,β-unsaturated-γ-ketoest...
Scheme 8: Intermediacy of γ-aryl-α,β-unsaturated-γ-hydroxyester during the reduction of γ-aryl-α,β-unsaturate...
Scheme 9: Reduction of γ-aryl-α,β-anti-dibromo-γ-ketoester with methanolic NaBH4.
Scheme 10: Intermediacy of γ-aryl-α,β-unsaturated-γ-hydroxyester during the reduction of γ-aryl-α,β-anti-dibro...
Scheme 11: Chemoselective reduction of keto group in the presence of ester moiety where structural rigidity pr...