Samarium‐Promoted Asymmetric Aldol–Tishchenko Reaction: Synthesis of Amino Acid‐Derived 4‐Amino‐1,3‐diols

Abstract

AbstractA samarium‐mediated novel synthesis of enantiopure 4‐amino‐1,3‐diols is carried out through a samarium‐promoted aldol–Tishchenko reaction starting from chiral α′‐amino‐α‐chloro ketones (derived from natural α‐amino acids) and aldehydes. The process takes place with moderate levels of stereoselectivity and in high yields. A mechanism is proposed to explain these results while the absolute configuration and structure of the aldol–Tishchenko adducts were established by X‐ray analysis. This method has also been utilized for the synthesis of enigmols, 1‐deoxysphingoid base analogues.