Chiral cinchona alkaloid-derived thiourea catalyst for enantioselective synthesis of novel β-amino esters by Mannich reaction

Chirality. 2012 Mar;24(3):223-31. doi: 10.1002/chir.21986. Epub 2012 Jan 25.

Abstract

A cinchona alkaloid-derived thiourea catalyst has been designed to access new asymmetric β-amino esters bearing benzothiazole moiety by utilizing a Mannich reaction between an imine and a malonate. A simultaneous activation of the two imine functionalities and malonate by the bifunctional chiral organocatalyst is proposed to account for the good yields (71-91%) and high enantiomeric excess (89.4-98.5%) under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic / methods*
  • Cinchona Alkaloids / chemistry*
  • Esters
  • Mannich Bases / chemistry*
  • Stereoisomerism
  • Substrate Specificity
  • Thiourea / chemistry*

Substances

  • Cinchona Alkaloids
  • Esters
  • Mannich Bases
  • Thiourea