Corey-Chaykovsky epoxidation of twisted amides: synthesis and reactivity of bridged spiro-epoxyamines

J Am Chem Soc. 2009 Sep 23;131(37):13246-7. doi: 10.1021/ja906471q.

Abstract

The first example of a Corey-Chaykovsky epoxidation employing amides as substrates is described. Medium-bridged twisted amides serve as precursors to a family of isolable aminoepoxides. The reactivity of bridged spiro-epoxyamines is also investigated.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemistry*
  • Amines / chemistry*
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry*
  • Spiro Compounds / chemistry*

Substances

  • Amides
  • Amines
  • Epoxy Compounds
  • Spiro Compounds