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Synthesis 1995; 1995(5): 527-532
DOI: 10.1055/s-1995-3960
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Palladium Assisted Alkylation-Insertion Reactions of Chiral Ene-Carbamates

Guy J. Laidig, Louis S. Hegedus*
  • *Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA, Fax +1(303)4915610; E-mail hegedus@lamar.colostate.edu
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Publication History

Publication Date:
31 December 2000 (online)

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Palladium(II) complexes of chiral ene-carbamate 2 underwent efficient, stereoselective alkylation by malonate carbanions having pendent unsaturated side chains. The resulting σ-alkylpalladium(II) complexes underwent efficient insertion of carbon monoxide to produce esters. Insertion of the pendent unsaturated groups was less efficient, and led to mixtures of insertion products with little stereoselectivity.

palladium-olefin alkylation - olefin insertion

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