Département de chimie moléculaire

By a selective three-component multi-catalytic sequence, amino-catalyzed oxa-Michael addition of oximes to alpha,beta-unsaturated aldehydes has been combined with a copper-catalyzed decarboxylative aldolization. This one-pot procedure enables the rapid construction of functionalized ketodiol scaffolds in 85 to 94% ee. Simple reduction of both the resulting oxime and ketone functions delivered the corresponding 1,3,5-triols of interest in a minimum of steps while considerably limiting waste generation. This methodology has been applied to the shortest (4 steps) synthesis of (+)-yashabushitriol, highlighting the synthetic potential of this new multi-catalytic sequence.