Isoborneol

Isoborneol

Isoborneol

Chemical compound

Isoborneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an exo position. The endo diastereomer is called borneol. Being chiral, isoborneol exists as enantiomers.

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Preparation

Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid in the presence of a strong acid catalyst.[2]

It can also be produced by reduction of camphor:

Isoborneol derivatives as chiral ligands

Derivatives of isoborneol are used as ligands in asymmetric synthesis.[3]

References

  1. [1]
    "(+)-Isoborneol". pubchem.ncbi.nlm.nih.gov. Retrieved 1 December 2022.
  2. [2]
    Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  3. [3]
    Yus, Miguel; Ramón, Diego (2007). "Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey". Synlett. 2007 (15): 2309–2320. doi:10.1055/s-2007-985602.
  4. [4]
    Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol". Organic Syntheses. 82: 87. doi:10.15227/orgsyn.082.0087.
  5. [5]
    White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(Dimethylamino)isoborneol". Organic Syntheses. 79: 130. doi:10.15227/orgsyn.079.0130.
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