Heterogeneous Dipeptide-Catalyzed α-Amination of Aldehydes in a Continuous-Flow Reactor: Effect of Residence Time on Enantioselectivity

Sándor B. Ötvös, Aliz Szloszár, I. Mándity, F. Fülöp

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A solid-supported dipeptide-catalyzed continuous-flow process was developed for the direct enantioselective α-amination of aldehydes with dibenzyl azodicarboxylate as the electrophilic nitrogen source. With residence time control as an efficient tool for the fine-tuning of the enantioselectivity, synthetically useful α-hydrazino alcohols were achieved with excellent ees. The packed-bed system proved to be highly robust: no decrease in catalyst activity or selectivity was detected throughout 20 h of continuous-flow operation.

Original languageEnglish
Pages (from-to)3671-3680
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number16-17
DOIs
Publication statusPublished - Nov 16 2015

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Keywords

  • asymmetric α-amination
  • continuous-flow reactor
  • organocatalysis
  • peptides
  • supported catalysts

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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