Trans-2-Phenyl-1-cyclohexanol
From Wikipedia, the free encyclopedia
- The correct title of this article is trans-2-Phenyl-1-cyclohexanol. The initial letter is shown capitalized due to technical restrictions.
trans-2-Phenyl-1-cyclohexanol is an organic compound. The two enantiomers of this compound are used in organic chemistry as chiral auxiliaries. The enantioselective synthesis was accomplished by J. K. Whitesell by adding Pseudomonas fluorescens lipase to racemic trans-2-phenylcyclohexyl chloroacetate. This enzyme is able to hydrolize the ester bond of the (-) enantiomer but not the (+) enantiomer. The (-)-cyclohexanol and the (+)-ester are separated by fractional crystallization and the isolated (+)-ester hydrolyzed to the (-)-cyclohexanol in a separate step.
The enantiomers have also been prepared by the Sharpless asymmetric dihydroxylation of 1-phenylcyclohexene to the diol followed by the selective reduction of the 1-hydroxyl group by Raney nickel.
[edit] References
- ^ Whitesell, J. K.; Chen, H. H.; Lawrence, R. M. J. Org. Chem. 1985, 50, 4663.
[edit] External links
- Enzyme procedure to trans-2-phenyl-1-cyclohexanol Organic Syntheses, Coll. Vol. 8, p.516 (1993); Vol. 69, p.1 (1990). Article
- Sharpless bishydroxylation procedure to trans-2-phenyl-1-cyclohexanol Organic Syntheses, Coll. Vol. 10, p.603 (2004); Vol. 79, p.93 (2002).Article
- Links to external chemical sources
