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Beilstein J. Org. Chem. 2016, 12, 1467–1475, doi:10.3762/bjoc.12.143
Graphical Abstract
Scheme 1: The three-stage mechanism for the specific acid-catalysed hydrolysis of cyclic orthoester A.
Figure 1: Hydroxonium catalytic coefficients (kH+ M−1 s−1 including standard errors where appropriate) for 1–...
Figure 2: Stereoelectronic contributions to hydrolysis; (a) conformationally constrained 1,3-dioxane orthoest...
Figure 3: The assignment of 10–11 and 14 via nOe [viewed C(4)→C(5)].
Figure 4: Newman projections of 9, 12 and 16 (viewed along Cβ→Cα).
Figure 5: Newman projections [viewed Cα–C(2)] of the preferred C2 arrangement of the 1,3-dioxolane ring depic...
Scheme 2: Isotopomers derived from C(4/5) hydrolytic attack of a generic 1,3-dioxolan-2-ylium cation B by H218...