Redox-Neutral 1,3-Diol Synthesis by Base-Promoted Diastereoselective Alcohol–Aldolization

In order to prepare
more efficiently key 1,3-diol fragments, we have devised a base-promoted
redox-neutral condensation of ketones with alcohols. This diastereoselective
alcohol–aldolization enables bypassing the classical oxidation
and reduction steps necessary for the preparation of this crucial
backbone by an overall redox-neutral formal borrowing hydrogen process.
The starting alcohols constitute both the precursors of the in situ
generated reactive aldehydes and the hydride source necessary for
the chemoselective reduction of the aldol adduct intermediates.