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Synlett 1998; 1998(2): 189-191
DOI: 10.1055/s-1998-1611
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Diastereoselective and Enantioselective Substitution Reactions of an Isoindoline-Borane Complex

Alexander J. Blake* , Mark R. Ebden, David N. A. Fox, Wan-Sheung Li, Nigel S. Simpkins
  • *Department of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD, U.K.; Fax (0115) 9513564; E-mail: Nigel.Simpkins@Nottingham.ac.uk
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Publication Date:
31 December 2000 (online)

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The alkylation of N-methylisoindoline-borane complex is diastereoselective, the substitution occurring predominantly syn to the borane group. Use of the SBuLi-sparteine reagent mixture enables the reaction to be conducted enantioselectively, giving the chiral isoindoline-borane complexes in up to 89% ee. Both the relative and absolute configurations of the alkylation products were established by X-ray structure determinations.

isoindoline - enantioselective metallation - (-)-sparteine - amine-borane complex