Figure 2.

Scope of amine-catalyzed remote hydroxylation. Isolated yields are provided apart from 3n, which was assayed by gas chromatrography using dodecane as an internal standard. Selectivities that are reported as precise ratios based on isolated yields of the relevant major and minor products, are based on NMR analysis of inseparable product mixture, or are based on GC analysis of the crude reaction mixture with the use of an internal standard and comparison to authentic samples. Selectivities that are reported as minimum ratios (e.g. 3b at ≥ 85:1 chemoselectivity) are provided when the relevant products (i.e. alcohol oxidation products or alternative oxidation sites) were not observed, and are provided as ratios of the major product to the unrecovered mass balance of the reaction. See Supporting Information for details.