Highly Stereoselective Synthesis of syn-1,3-Diols through a Sequential Titanium-Mediated Aldol Reaction and LiBH4 Reduction

A sequential transformation based on a titanium-mediated aldol reaction from chiral alpha-tert-butyldimethylsilyloxy ketones followed by reduction of the resultant aldolates with LiBH4 provides a straightforward access to syn-1,3-diols. These diols, containing up to three new stereocentres, be easily isolated in high yields after a simple work-up without any additional oxidative treatment, which confers to this procedure an appealing position to prepare stereoselectively such sort of structures.