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

[Display omitted] 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 d...

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Bibliographic Details
Published in:Tetrahedron letters 2004-12, Vol.45 (51), p.9469-9474
Main Authors: Coumbarides, Gregory S., Eames, Jason, Ghilagaber, Stephanos, Suggate, Michael J.
Format: Article
Language:English
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.10.090