Frans-2-Phenylcyclohexanol

Enanfiomerically pure frans-2-phenylcyclohexanol, firsf used by Whifesell as a chiral auxiliary has become a popular reagenf in a number of asymmefric fransformafions. Some recent applications include asymmetric azo-ene reactions, [4 + 2]-cycloaddition reactions, ketene-olefin [2 + 2]-reactions, enolate-imine cyclocondensations,Pauson-Khand reactions," palladium annulations and Reformatsky reactions. Despite its potential, use of fhis chiral auxiliary on a preparafive scale is currenfly limifed by ifs prohibitive cost. 

Another approach to the stoichiometric enantioselective Pauson-Khand reaction involves the use of chiral auxiliaries. Extensive investigations on this subject have been carried out by Periods, Moyano, Greene, and coworkers. Initial reports detailed the use of frans-2-phenylcyclohexanol as a chiral auxiliary for the... 

SnCU-catalyzed ene reactions of frans-2-phenylcyclohexyl glyoxylate (60) also proceed with very high asymmetric induction.43 Since both enantiomers of frms-2-phenylcyclohexanol are readily available, this chiral auxiliary has practical advantages. SnCU-catalyzed reaction of (60) with diene (61) gives... 

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