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Synlett 2001; 2001(Special Issue): 0927-0930
DOI: 10.1055/s-2001-14626
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Enantioselective Copper-Catalyzed SN2′ Substitution with Grignard Reagents

Alexandre Alexakis* , Christophe Malan, Louise Lea, Cyril Benhaim, Xavier Fournioux
  • *Chimie Organique, Sciences II, University of Geneva, Quai Ernest Ansermet, CH-1211, Geneva, Switzerland; Fax + 41 22 3 28 73 96; E-mail: Alexandre.Alexakis@chiorg.unige.ch
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Publikationsdatum:
31. Dezember 2001 (online)

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Cinnamyl chlorides undergo selective SN2′ allylic substitution by Grignard reagents using catalytic amount (1 mol%) of CuCN and 1-2 mol% trivalent phosphorus ligands, in dichloromethane. With chiral phosphorus ligands derived from TADDOL ee's up to 73% could be obtained.

chiral phosphorus ligands - copper - asymmetric catalysis - SN2′ - TADDOL