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
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