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Synthesis 1997; 1997(12): 1394-1398
DOI: 10.1055/s-1997-1382
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Convenient Synthesis of Enantiomerically Enriched β-Cyclopropylalaninol Derivatives by Kinetic Resolution via (-)-Sparteine-Mediated Deprotonation

Thomas Hense, Dieter Hoppe*
  • *Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany, Fax +49(251)8339722
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Publication Date:
31 December 2000 (online)

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The racemic mixture of the protected β-cyclopropylalaninol derivative 11 was subjected to asymmetric deprotonation by means of sec-butyllithium/(-)-sparteine, resulting in a preferential abstraction of the α-pro-S-H in (R)-11; (S)-11 remains untouched.

amino alcohol - sparteine - kinetic resolution - enantioselective deprotonation