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Synlett 1993; 1993(10): 726-728
DOI: 10.1055/s-1993-22585
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Kinetic Resolution of β-Stereogenic O-Alkyl Carbamates by (-)-Sparteine-Assisted Deprotonation. External versus Internal Chiral Induction.

Jan Haller* , Thomas Hense, Dieter Hoppe
  • *Institut, für Organische Chemie, Westfälische Wilhelms-Universität Münster, Orléansring 23, D-48149 Münster, Germany
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Publication Date:
19 March 2002 (online)

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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.