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Isoborneol
Chemical compound From Wikipedia, the free encyclopedia
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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]
- (2S)-(−)-3-exo-(morpholino)isoborneol or MIB[4] with a morpholine substituent in the α-hydroxyl position.
- (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[5] with a dimethylamino substituent in the α-hydroxyl position
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References
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