trans-2-Phenyl-1-cyclohexanol

(1S,2R)-2-phenylcyclohexanol
IUPAC name

(1S,2R)-2-phenyl-1-cyclohexanol
Identifiers
CAS number 34281-92-0
PubChem 9898975
ChemSpider 8074632 Y
Jmol-3D images Image 1
Properties
Molecular formula C12H16O
Molar mass 176.25 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

trans-2-Phenyl-1-cyclohexanol is an organic compound. The two enantiomers of this compound are used in organic chemistry as chiral auxiliaries.

Preparation

The enantioselective synthesis was accomplished by J. K. Whitesell by adding Pseudomonas fluorescens lipase to racemic trans-2-phenylcyclohexyl chloroacetate.[1][2] This enzyme is able to hydrolyze 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.[3]

References

  1. ^ J. K. Whitesell, H. H. Chen and R. M. Lawrence (1985). "trans-2-Phenylcyclohexanol. A powerful and readily available chiral auxiliary". J. Org. Chem. 50 (23): 4663–4664. doi:10.1021/jo00223a055. 
  2. ^ A. Schwartz, P. Madan, J. K. Whitesell, and R. M. Lawrence (1993), "Lipase-Catalyzed Kinetic Resolution of Alcohols via Chloroacetate Esters: (−)-(1R,2S)-Trans-2-Phenylcyclohexanol And (+)-(1S,2R)-Trans-2-Phenylcyclohexanol", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0516 ; Coll. Vol. 8: 516 
  3. ^ Javier Gonzalez, Christine Aurigemma, and Larry Truesdale (2004), "Sharpless bishydroxylation procedure to trans-2-phenyl-1-cyclohexanol", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=V79P0093 ; Coll. Vol. 10: 603