A Simple Procedure for the Preparation of Chiral ‘Tris(hydroxymethyl)methane’ Derivatives

The aldol adducts 1a–13a of R,R‐2(tertbutyl)‐6‐methyl‐1,3‐dioxan‐4‐one (from 3‐hydroxybutanoic acid) to aldehydes, single diastereoisomers obtained as described previously, are acetylated or benzoylated to the corresponding esters 1b–5b and 6c–13c, respectively, which in turn are reduced with LiAlH4 to the title compounds 14–24. The enantiomerically pure triols thus available may be useful as chiral building blocks, as auxiliaries for enantioselective reactions, and as center pieces for chiral dendrimers.