Chiral auxiliary also 2-phenylcyclohexanol

Optically pure trans-2-phenylcyclohexanol can also be prepared by resolution of the phthalate esters using brucine to obtain the (-t-)-alcohol and strychnine to obtain the (-)-alcohol (after basic hydrolysis of their respective salts).11 Enzyme-catalyzed kinetic resolution of the acetate esters using pig liver esterase4 and pig liver acetone powder12 has been used to prepare both enantiomers of this chiral auxiliary. The hydroboration of 1-phenylcyclohexene with isopinocampheylborane has been reported to give the chiral auxiliary in 97% enantiomeric excess.13... 

Substantial progress has also been made in the chiral auxiliary-based approach to an enantioselective intermolecular Pauson-Khand reaction. Initial studies utilizing alkynes substituted with fra s-2-phenylcyclohexanol produced cyclopentenones with low drs, however, the diastereomers were easily separable... 

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

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