1228099-67-9Relevant academic research and scientific papers
Short and Atom-Economic Enantioselective Synthesis of the σ1-Receptor Ligands (S)- And (R)-Fluspidine - Important Tools for Positron Emission Tomography Studies
Bunse, Paul,Schlepphorst, Christoph,Glorius, Frank,Kitamura, Masato,Wünsch, Bernhard
, p. 13744 - 13754 (2019)
Aryl bromides 2a and 2b bearing an alkynyl substituent in the o-position reacted with n-butyllithium and 1-benzylpiperidin-4-one in a one-pot Domino reaction to form ester 3 and aldehyde 5, respectively. Enantiomeric alcohols (R)-8 and (S)-8 were obtained by conjugate NaBH4 reduction of α,β-unsaturated ester 3 in the presence of chiral cocomplexes (R,R)-10 and (S,S)-10. Starting from orthoester 2a, the precursors (R)-8 and (S)-8 for the synthesis of fluspidine enantiomers (R)-1/[18F](R)-1 and (S)-1/[18F](S)-1 were obtained in only two reaction steps without additional steps for N-protection in an atom-economic manner in 95.6% ee and 97.2% ee, respectively.
