CHIRAL OXIMES IN ASYMMETRIC-SYNTHESIS - ADDITION OF ORGANOMETALLIC REAGENTS TO O-(1-PHENYLETHYL) ALDOXIMES

D S BROWN, P T GALLAGHER, A P LIGHTFOOT, C J MOODY, A M Z SLAWIN, E SWANN

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42 Citations (Scopus)

Abstract

Addition of Grignard and organolithium reagents to O-(1-phenylethyl) aldoximes in the presence of boron trifluoride etherate gives secondary hydroxylamines in 21-84% yield with up to 95% diastereomeric excess.

Original languageEnglish
Pages (from-to)11473-11488
Number of pages16
JournalTetrahedron
Volume51
Issue number42
Publication statusPublished - 16 Oct 1995

Keywords

  • ALDEHYDE-SAMP HYDRAZONES
  • ALPHA-IMINO ESTERS
  • SODIUM-BOROHYDRIDE
  • ORGANOLITHIUM REAGENTS
  • AMINO-ACIDS
  • ETHERS
  • REDUCTION
  • CHLORIDE

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