We report the chiral‐auxiliary‐controlled diastereoconvergent allylation reactions of allyltrimethylsilane with diastereomeric mixtures of diarylmethanols in the presence of FeCl3 as a Lewis acid catalyst. This reaction was successfully applied to a variety of substrates; it proceeded irrespective of the substituent on the aromatic ring of the substrate. The present method was used as the key step in synthesizing (R)‐tolterodine.
The reaction system of a Reformatsky reagent as a promoter and EtOAc as a solvent and acetyl donor was found to achieve efficient acetylation of a variety of primary and secondary aliphatic alcohols under mild conditions. The reaction can be carried out by a simple one-pot operation and does not require heating. The reaction shows a high tolerance for various functional groups and chemoselectivity, such that the phenolic hydroxyl groups do not react. Furthermore, the reaction can be used for gram-scale acetylation.
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