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Alpine borane : ウィキペディア英語版
Alpine borane

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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:〔M. Mark Midland "B-3-Pinanyl-9-borabicyclo()nonane" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley, New York.. Article Online Posting Date: April 15, 2001〕
: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.
==Related reagents==
A range of alkyl-substituted derivatives of borane and diborane are specialty reagents in organic synthesis. Two such reagents that are closely related to Alpine borane are 9-BBN and diisopinocampheylborane.

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