Asymmetric Induction during the Reactions of Dienyl-Iron and Diene-Molybdenum Complexes with Chiral N-Acyloxazolidinone Enolates

Article abstract of DOI:10.1021/jo00282a035

The addition of chiral N-acyloxazolidinone enolates to diene-molybdenum and dienyl-iron complexes gives enantiomeric excesses as high as 80percent.The oxazolidinone derived from valinol adds preferentially to the pro-S terminus of the diene/dienyl complex while the oxazolidinone derived from norephedrine adds to the pro-R terminus.A rationalization of these experimental results is attempted based on Seebach's topological rules for the Michael addition of enamines to nitro olefins.