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Synlett 2001; 2001(Special Issue): 1013-1015
DOI: 10.1055/s-2001-14649
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Regioselective Ring Opening of Enantiomerically Enriched Epoxides via Catalysis with Chiral (Salen)Cr(III) Complexes

Bridget D. Brandes* , Eric N. Jacobsen
  • *Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA; Fax (617) 496-1880
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Publication Date:
31 December 2001 (online)

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Chiral (salen)chromium(III)N3 complexes are demonstrated to be catalysts for the regioselective ring opening a variety of enantiomerically enriched epoxides. Selective nucleophilic attack at either epoxide carbon atom can be achieved by selection of the appropriate enantiomer of catalyst. A highly selective synthesis of norpseudoephedrine is described using this strategy.

regioselectivity - ring opening - (salen)Cr(III) complexes - epoxides