• (+)-(Ipc₂BAll)

  [85116-38-7] C₂₃H₃₉B (MW 324.36)

  InChI = 1S/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m1/s1

  InChIKey = ZIXZBDJFGUIKJS-RLEROFIGSA-N

• (−)-(Ipc₂BAll)

  [106356-53-0]

  InChI = 1S/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m0/s1

  InChIKey = ZIXZBDJFGUIKJS-AXSQLCHVSA-N

(reagent for the asymmetric allylboration of aldehydes to produce homoallylic alcohols^{2, 3})

Solubility: most often used as the crude preparation in Et₂O; however, reactions have also been conducted in CS₂, CHCl₃, CH₂Cl₂, toluene, and THF.

Analysis of Reagent Purity: ¹¹B NMR (δ +78, diethyl ether).

Preparative Methods: prepared in three steps from either (+)- or (−)-α-pinene (eq 1) (see also B‐Methoxydiisopinocampheylborane).

(1)

Handling, Storage, and Precautions: removal of magnesium salts from the crude reagent preparation is accomplished by solvent exchange into pentane and filtration. Concentration in vacuo provides the neat allylborane as a colorless liquid that can be stored under argon atmosphere for an extended period of time.