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Kinetic Resolution of β-Stereogenic<i>O</i>-Alkyl Carbamates by (-)-Sparteine-Assisted Deprotonation. External versus Internal Chiral Induction.
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1993
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Methyl CarbamateEngineeringBiochemistryInternal Chiral InductionKinetic ResolutionNatural SciencesDiversity-oriented SynthesisOrganic ChemistryPro-s ProtonChemistryPhenylpropyl CarbamateStereoselective SynthesisAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
The chiral base s-butyllithium / (-)-sparteine recognizes the (R)-enantiomer in a 2 phenylpropyl carbamate and the (S)-enantiomer in a 1-(1,2,3,4-tetrahydronaphthyl)methyl carbamate. In addition with its high preference for the pro-S proton, highly diastereoselective electrophilic substitutions in the α-position of R-phenylalkanols, combined with efficient kinetic resolution of the racemate, are achieved.