1383618-08-3Relevant academic research and scientific papers
Samarium-promoted asymmetric aldol-Tishchenko reaction: Synthesis of amino acid-derived 4-amino-1,3-diols
Rodriguez-Solla, Humberto,Concellon, Carmen,Tuya, Paula,Garcia-Granda, Santiago,Diaz, M. Rosario
, p. 1679 - 1684 (2012/09/05)
A 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. Copyright
