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Isoborneol

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.

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.

It can also be produced by reduction of camphor: :[[File:(1R,4R)-Camphor Reduction V.1.svg|frameless|420 px]]

Isoborneol derivatives as chiral ligands

Derivatives of isoborneol are used as ligands in asymmetric synthesis.

  • (2S)-(−)-3-exo-(morpholino)isoborneol or MIB with a morpholine substituent in the α-hydroxyl position.
  • (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB with a dimethylamino substituent in the α-hydroxyl position

References

References

  1. "(+)-Isoborneol".
  2. (2006). "Kirk-Othmer Encyclopedia of Chemical Technology".
  3. (2007). "Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey". Synlett.
  4. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol". Organic Syntheses.
  5. (2002). "(2S)-(−)-3-exo-(Dimethylamino)isoborneol". Organic Syntheses.
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secondary-alcohols monoterpenes bicyclic-compounds cyclopentanes
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