The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.

: The application of the "supersilyl” group as carboxylic acid protecting group has been investigated. The unique properties of the “supersilyl” group enabled it to outperform typical carboxyl protecting groups, conferring extraordinary protection upon the carboxyl functionality. “Supersilyl” esters were also utilized for the first time as stable carboxylic acid synthetic equivalents in highly stereoselective aldol and Mannich reactions. The value of this methodology has been further described by the easy photo-deprotection protocol and its applications in rapid synthesis of polyketide subunits.