Synthesis of 2-amino-1,3-diols incorporating the cyclobutane ring

The synthesis of free and protected 2-amino-1,3-diols with threoninol substructure that incorporate a conformational restriction defined by the cyclobutane ring is reported. The key step in the synthesis of these target compounds, namely cis- and trans-c4-threoninols, is the addition of methylmagnesium bromide to a cyclobutanone derivative. The selectivity of the reaction is modulated by the solvent.