β‐Hydroxy‐tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE‐412

A new synthetic protocol provides a simple and direct method to generate functionalized β‐hydroxy‐tetrahydroquinolines (THQs). Hydroboration of quinolines using chloroboranes followed by oxidation with NaBO 3 ⋅H 2 O led to the formation of functionalized β‐hydroxy THQs. High regio‐ and diastereoselectivities were observed in α and γ substituted quinolines and the trans diastereomer of the β‐hydroxy‐THQ was the major isostere. This new protocol was utilized to build the novel antibody‐targeted lupus peptidomimetic, FISLE‐412 .