Oxidation of chiral α-phenylacetate derivatives: formation of dimers with contiguous quaternary stereocenters versus tertiary alcohols

The menthol esters of α-phenylacetate derivatives undergo diastereoselective oxidative dimerizations (α-cyano) in the presence of oxidants, and nitrosylation (α-amido) in the presence of CAN to form products containing adjacent functionalized quaternary stereocenters and tertiary alcohols, respectively.

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(2R,3S)-Bis(2-isopropyl-5-methylcyclohexyl) 2,3-dicyano-2,3-diphenylsuccinateC38H48N2O4[α]D23=-45.1 (c 0.61, CHCl3)

(2R,3S)-Bis(2-isopropyl-5-methylcyclohexyl) 2,3-dicyano-2,3-dip-tolylsuccinateC40H52N2O4[α]D23=-50.2 (c 0.96, CHCl3)

(2S,3S)-Bis(2-isopropyl-5-methylcyclohexyl) 2,3-dicyano-2,3-dip-tolylsuccinateC40H52N2O4[α]D23=-148.5 (c 0.90, CHCl3)

(2S)-2-Isopropyl-5-methylcyclohexyl 3-amino-2-hydroxy-3-oxo-2-phenylpropanoateC19H27NO4[α]D23=-88.7 (c 0.62, CHCl3)

(5S)-2-Isopropyl-5-methylcyclohexyl 2,2-dimethyl-4-oxo-5-phenyloxazolidine-5-carboxylateC22H31NO4[α]D23=-53.4 (c 0.72, CHCl3)

(R)-2,3-Dihydroxy-N-isopropyl-2-phenylpropanamideC12H17NO3[α]D23=+3.5 (c 0.38, CHCl3)