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Synthesis 1988; 1988(5): 362-366
DOI: 10.1055/s-1988-27574
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Diastereoselective Construction of α-Quaternary Carbon Centers in the Chiral-Auxiliary-Mediated Aza-Claisen Rearrangement of Ketene N-Allyl-N,O-acetals

Mark J. Kurth* , Edward G. Brown
  • *Department of Chemistry, University of California, Davis, CA 95616, USA
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Publication Date:
20 August 2002 (online)

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The aza-Claisen rearrangement of ketene N-allyl-N,O-acetals has been applied to the diastereoselective construction of precursors of 2-quaternary 4-pentenoic acids (82-97% ds). Best yields are obtained when alkoxides are used to deprotonate the intermediate oxazolinium salts.

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