Bifunctional-Benzothiadiazine-Catalyzed Regio- and Stereoselective Aldol Reactions Using A 1,3-Acetonedicarboxylic Acid Monoester

Abstract

Regio-and stereoselective decarboxylative aldol reactions of a 1,3-acetonedicarboxylic acid monoester were achieved using an aminobenzothiadiazine organocatalyst. The products were obtained with perfect regioselectivity and moderate to good enantioselectivity using various aromatic aldehydes. Subsequently, the thus obtained adducts were efficiently converted various chiral building blocks.Chiral β,δ-dihydroxycarboxylic acid moieties represent an important structural motif in various pharmaceuticals and bioactive natural products (Scheme 1a). [1][2][3][4] For example, atorvastatin, which inhibits