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Synlett 1998; 1998(10): 1165-1167
DOI: 10.1055/s-1998-5741
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Enantioselective Nucleophilic Opening of meso Epoxides by Organolithium Reagents

Alexandre Alexakis* , Emmanuel Vrancken, Pierre Mangeney
  • *Department of Organic Chemistry, Université P. et M. Curie, T44-45, case 183, 4 place Jussieu, Paris 75005, France; Fax 33 1 44 27 75 67; E-mail: alexakis@moka.ccr.jussieu.fr
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Publication Date:
31 December 2000 (online)

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Aryl lithium reagents, complexed with (-)-sparteine, react enantioselectively with cyclic meso epoxides, to afford chiral aryl cyclanols. The enantiomeric excess, though moderate (27-87%), is the best in the literature for such a reaction. Activation by BF3 ⋅ OEt2 is needed, and is compatible with a diamine such as (-)-sparteine.

epoxides - organolithium reagents - BF3 ⋅ Et2O activation - (-)-sparteine

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