Electroauxiliary-assisted sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen: application to the synthesis of spiro compounds

J Am Chem Soc. 2002 Dec 18;124(50):14824-5. doi: 10.1021/ja028663z.

Abstract

The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amines / chemistry
  • Carbamates / chemistry
  • Electrochemistry
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Spiro Compounds / chemical synthesis*

Substances

  • Amines
  • Carbamates
  • Pyrrolidines
  • Spiro Compounds