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Synlett 1993; 1993(10): 726-728
DOI: 10.1055/s-1993-22585
DOI: 10.1055/s-1993-22585
letter
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Kinetic Resolution of β-Stereogenic O-Alkyl Carbamates by (-)-Sparteine-Assisted Deprotonation. External versus Internal Chiral Induction.
Further Information
Publication History
Publication Date:
19 March 2002 (online)
![](https://www.thieme-connect.de/media/synlett/199310/lookinside/thumbnails/10.1055-s-1993-22585-1.jpg)
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.