Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

J Org Chem. 2011 Jan 21;76(2):358-72. doi: 10.1021/jo1018816. Epub 2010 Dec 29.

Abstract

Ethyl- (7), benzyl- (8), tert-butyl- (9), and fluorenylmethyl-4-chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry*
  • Carbamates / chemistry*
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Hydroxylation
  • Indicators and Reagents / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitrogen / chemistry*
  • Stereoisomerism
  • Ultraviolet Rays

Substances

  • Alkanes
  • Carbamates
  • Indicators and Reagents
  • Nitrogen