Diisopinocampheylborane

Diisopinocampheylborane

Structure of (+)-Diisopinocampheylborane dimer
Names
IUPAC name
Di[(1S,2R,3S,5S)-pinan-3-yl]borane
Systematic IUPAC name
Bis[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
Other names
(+)-Di-3-pinanylborane; Diisopinocampheylborane; Ipc2BH dimer
Identifiers
3D model (JSmol)
Abbreviations Ipc2BH
ChemSpider
  • InChI=1S/C20H35B/c1-11-15-7-13(19(15,3)4)9-17(11)21-18-10-14-8-16(12(18)2)20(14,5)6/h11-18,21H,7-10H2,1-6H3
    Key: KBGJOMVTAXYPAG-UHFFFAOYSA-N
  • InChI=1/C20H35B/c1-11-15-7-13(19(15,3)4)9-17(11)21-18-10-14-8-16(12(18)2)20(14,5)6/h11-18,21H,7-10H2,1-6H3
    Key: KBGJOMVTAXYPAG-UHFFFAOYAB
  • [H]B(C1CC2CC(C1(C))C2(C)(C))C3CC4CC(C3(C))C4(C)(C)
Properties
C20H35B
Molar mass 286.31 g·mol−1
Appearance Colorless solid
Density 1.044 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis. This colourless solid is the precursor to a range of related reagents. The compound was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes. The reagent is mainly used for the synthesis of chiral secondary alcohols. The reagent is often depicted as a monomer but like most hydroboranes, it is dimeric with B-H-B bridges.[1]

  1. ^ Fürstner, Alois; Bonnekessel, Melanie; Blank, Jarred T.; Radkowski, Karin; Seidel, Günter; Lacombe, Fabrice; Gabor, Barbara; Mynott, Richard (2007). "Total Synthesis of Myxovirescin A1". Chemistry – A European Journal. 13 (31): 8762–8783. doi:10.1002/chem.200700926. PMID 17768720.