Chemistry Letters, Vol.36, No.2, 276-277, 2007
Azaspirovesamicols-regioselective synthesis and crystal structure analysis of a novel class of vesamicol analogues as potential ligands for the vesicular acetylcholine transporter
This report describes the high regioselectivity of nucleophilic epoxide ring-opening reactions which resulted in two of four possible regioisomers of N-benzoyl- (5a and 5b) and N-fluoro-benzoylazaspirovesamicol derivatives (6a and 6b), respectively. Based on structural information obtained from X-ray crystal structure analyses of 5a and 5b the mode of epoxide ring-opening is discussed.