Dynamic kinetic resolution of atropisomeric amides

Org Lett. 2004 Jun 10;6(12):2051-3. doi: 10.1021/ol0492952.

Abstract

[reaction: see text] Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Hydrogen Bonding
  • Kinetics
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Amides