Enantioselective C--C bond formation to sulfonylimines through use of the 2-pyridinesulfonyl group as a novel stereocontroller

Chemistry. 2008;14(7):2145-52. doi: 10.1002/chem.200701425.

Abstract

Enantioselective C--C bond formation to 2-pyridinesulfonylimines afforded products with good enantioselectivity. Dynamic induction of chirality on the sulfur by coordination of a chiral Lewis acid to the pyridine nitrogen and one of the prochiral sulfonyl oxygens induces enantioselectivity. Since the 2-pyridinesulfonyl group can easily be removed after the reaction, it acts not only as an activating group but also as an efficient stereocontroller.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Molecular Structure
  • Pyridines / chemistry*
  • Stereoisomerism
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry*

Substances

  • Imines
  • Pyridines
  • Sulfones
  • Carbon