trans-2-Phenyl-1-cyclohexanol

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(1S,2R)-2-phenylcyclohexanol
(1S,2R)-2-phenylcyclohexanol-2D-skeletal.png
Names
IUPAC name
(1S,2R)-2-phenyl-1-cyclohexanol
Identifiers
3D model (JSmol)
ChemSpider
Properties
C12H16O
Molar mass 176.259 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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[edit]

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]

trans-2-Phenyl-1-hexanol enantiomers in chair conformations

References[edit]

  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". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 8, p. 516
  3. ^ Javier Gonzalez, Christine Aurigemma, and Larry Truesdale (2004). "Sharpless bishydroxylation procedure to trans-2-phenyl-1-cyclohexanol". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 10, p. 603