527680-81-5Relevant academic research and scientific papers
Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes
Granander, Johan,Sott, Richard,Hilmersson, Goeran
, p. 439 - 447 (2007/10/03)
Six chiral amino sulfides have been synthesised from the amino acids phenylalanine, phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with benzaldehyde, resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of >98.5 and 95%, respectively. These stereoselectivities were significantly higher than those induced by the ether analogues.
