Stereoselective synthesis of skipped polyols by substrate-directed asymmetric induction
[formula: see text] A series of C2- or sigma-symmetric oligo-1,3-dioxanylmethanes, 2-5, have been prepared using a bidirectional approach. In bidirectional syntheses of meso compounds, only substrate-based asymmetric induction could be applied. 1,3-Asymmetric induction in Mukaiyama-aldol additions, 1,5-asymmetric induction in enol-borinate aldol reactions, and 1,3-anti-selective reduction of aldols turned out to be reliable tools in the preparation of compounds 3-5.
Trieselmann
T
Fachbereich Chemie der Philipps-Universitat, Marburg, Germany.
Hoffmann
RW