199661-76-2Relevant academic research and scientific papers
Asymmetric synthesis of CDP840 by Jacobsen epoxidation. An unusual syn selective reduction of an epoxide
Lynch,Choi,Churchill,Volante,Reamer,Ball
, p. 9223 - 9228 (1997)
An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the 'skewed side-on approach model' proposed by Jacobsen. LiBH4 · BH3 reduction of the epoxides was found to proceed with retention of configuration.
