Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. This reagent is generated by treating 9-BBN with α-pinene to give a sterically crowded trialkylborane. The resulting chiral species can stereoselectively reduce ketones, aldehydes, even deutero aldehydes in what is known as the Midland Alpine Borane Reduction, or simply the Midland Reduction:
- C8H12B-pinanyl + RCDO → C8H12BOCHDR + (+)-d-pinene
Hydrolysis of the resulting borinic ester affords the alcohol:
- C8H12BOCHDR + H2O → C8H12BOH + HOCHDR
It is also effective for the stereoselective reduction of certain acetylenic ketones.
Read more about Alpine Borane: Related Reagents
Famous quotes containing the word alpine:
“Reason now gazes above the realm of the dark but warm feelings as the Alpine peaks do above the clouds. They behold the sun more clearly and distinctly, but they are cold and unfruitful.”
—G.C. (Georg Christoph)