Electroreductive intramolecular coupling of aromatic imino esters: is four-membered cyclization much more favorable than six-membered cyclization?

Org Lett. 2006 Mar 30;8(7):1323-5. doi: 10.1021/ol053144x.

Abstract

[reaction: see text] The electroreduction of an aromatic imino ester prepared from (S)-glutamic acid in the presence of chlorotrimethylsilane and triethylamine afforded a four-membered cyclized product, a mixed ketal of cis-2,4-disubstituted azetidine-3-one, stereospecifically. Calculations for the transition states by the DFT method support the predominant formation of the azetidine. The electroreduction of an aromatic imino ester prepared from (S)-aspartic acid gave almost equal amounts of a diastereomerically pure mixed ketal of cis-2,4-disubstituted azetidine-3-one and a diastereomeric mixture of 2,5-disubstituted pyrollidine-3-one.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / chemistry
  • Azetidines / chemical synthesis*
  • Azetidines / chemistry
  • Cyclization
  • Esters
  • Glutamic Acid / chemistry*
  • Imines / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Pyrrolidinones / chemical synthesis*
  • Pyrrolidinones / chemistry
  • Stereoisomerism

Substances

  • Azetidines
  • Esters
  • Imines
  • Pyrrolidinones
  • Aspartic Acid
  • Glutamic Acid