Abstract
Novel cis‐ and trans‐2‐(p‐bromophenyl)‐5‐methylthiazolidin‐4‐ones, S,N‐containing heterocyclic compounds, were provided in a cis‐stereocomplementary and trans‐stereocomplementary synthetic manner. cis‐Selective cyclo‐condensation proceeded between 2‐sulfanylpropanoic acid (thiolactic acid) and an imine derived from 4‐bromobenzaldehyde and methylamine, whereas Ti(OiPr)4 and Ti(OiBu)4‐promoted trans‐selective cyclo‐condensation proceeded between benzyl 2‐sulfanylpropanoate and the imine. The obtained cis‐ and trans‐2‐(p‐bromophenyl)‐5‐methylthiazolidin‐4‐ones were successfully converted to 2‐(3‐furyl)phenyl derivatives and bis(pinacolato)diborane derivatives utilizing Suzuki–Miyaura and Miyaura–Ishiyama cross‐coupling reactions, respectively, in an umpolung manner.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
