Chiral copper(II) complex-catalyzed reactions of partially protected carbohydrates

Org Lett. 2013 Dec 20;15(24):6178-81. doi: 10.1021/ol4033072. Epub 2013 Nov 26.

Abstract

Catalyst-controlled regioselective functionalization of partially protected saccharide molecules is a highly important yet under-developed area of carbohydrate chemistry. Such reactions allow for the reduction of protecting group manipulation steps required in syntheses involving sugars. Herein, an approach to these processes using enantiopure copper-bis(oxazoline) catalysts to control couplings of electrophiles to various partially protected sugars is reported. In a number of cases, divergent regioselectivity was observed as a function of the enantiomer of catalyst that is used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemical synthesis*
  • Carbohydrates / chemistry
  • Catalysis
  • Copper / chemistry*
  • Molecular Conformation
  • Organometallic Compounds / chemistry*

Substances

  • Carbohydrates
  • Organometallic Compounds
  • Copper