Investigations into the enantioselective C-protonation of prostereogenic enolate(s) derived from N,N′-diisopropyl-2-phenylpropanamide using suicide C-based proton sources

  • Coumbarides G
  • Eames J
  • Ghilagaber S
 et al. 
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Abstract

The synthesis of enantiomerically enriched (-)-(R)-N, N′-diisopropyl- 2-phenylpropanamide was achieved in up to 69% enantiomeric excess by symmetrisation of the corresponding racemic amide by addition of sec-BuLi (to give the corresponding achiral lithium enolate) and subsequent desymmetrisation by the addition of a chiral C-based proton source. We discuss potential factors that may be responsible for this observed enantioselectivity and comment on the role of the chiral acid. © 2004 Elsevier Ltd. All rights reserved.

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Authors

  • Gregory S. Coumbarides

  • Jason Eames

  • Stephanos Ghilagaber

  • Michael J. Suggate

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