text: Because of the large size of the α-pinenyl substituents, diisopinocampheylborane only hydroborates unhindered alkenes.  These reactions proceed with high enantioselectivity. 2-Butene, 2-pentene, 3-hexene are converted to the respective chiral alcohols in high ees.  Norbornene under the same conditions gave an 83% ee.  Heterocycles (dihydrofuran, dihydrothiophene, dihydropyrrole, tetrahydropyran) give the alcohols in ≥99% ee; the high ees reflect their constrained conformations.
  It adds to alkynes to form the corresponding vinyldiisopinocampheylboranes
  In a highly stereoselective reaction, allyldiisopinocampheylboranes converts aldehydes to the homologated alcohols, rapidly even at -100 °C. The alkyldiisopinocampheylboranes, which result from the addition to alkenes, usefully react with a range of different reagents.  Hydroxylamine-O-sulfonic acid  provides 3-pinanamine.
  Also useful is the reaction of diisopinocampheylborane with an aldehyde (RCHO) to give the chiral boronic ester, (isopinocampheyl)BOCH(R), which can be further used is a number of reactions e.g. Suzuki reaction.