Asymmetric aldol reaction in a continuous-flow reactor catalyzed by a highly reusable heterogeneous peptide

Sándor B. Ötvös, István M. Mándity, Ferenc Fülöp

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A solid-supported peptide-catalyzed continuous-flow (CF) process was developed for asymmetric aldol reactions. The catalyst was readily synthesized and immobilized by solid-phase peptide synthesis (SPPS) on a swellable polymer support in one single step. Ignoring the peptide cleavage from the resin means no work-up, no purification, and no product loss. After thorough optimization of the reaction conditions, synthetically useful β-hydroxyketone products were obtained in high yields and stereoselectivities. It was found that the heterogeneous catalytic reaction is diffusion-controlled under the present conditions; thus, elevation of the pressure is necessary to maximize conversion of the flow process. Besides being simple and efficient, the described method is also rapid and promisingly productive, with short residence times on the catalyst bed. The immobilized peptidic catalyst is highly recyclable, while further advantageous features are the ease of product isolation and the possibility of facile scale-up, furnishing sustainable catalytic methodology.

Original languageEnglish
Pages (from-to)179-185
Number of pages7
JournalJournal of Catalysis
Volume295
DOIs
Publication statusPublished - Nov 1 2012

Keywords

  • Aldol reaction
  • Continuous-flow process
  • Heterogeneous catalysis
  • Organocatalysis
  • Packed bed reactor
  • Peptides
  • Pressure
  • Supported catalysts

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Asymmetric aldol reaction in a continuous-flow reactor catalyzed by a highly reusable heterogeneous peptide'. Together they form a unique fingerprint.

  • Cite this