New developments in enantioselective bronsted acid catalysis: Chiral ion pair catalysis and beyond

M. Rueping*, E. Sugiono

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingConference contributionpeer-review

Abstract

The design of catalytic reactions that proceed with high enantioselectivity is an important goal in organic synthesis. Increased interest in this research area has resulted in substantial progress, particularly in the field of metal catalyzed transformations. In recent years small organic molecules have been used as organocatalysts for a variety of enantioselective reactions. Among these, secondary amine catalysts are the most widely applied and can be used in the activation of the nucleophilic component through enamine formation (enamine catalysis), or by formation of an iminum intermediate to activate the electrophile (iminium catalysis). Additionally, chiral diols and thioureas, as well as carbene- and DMAP-derivatives (hydrogen bonding, nucleophilic catalysis), have been shown to be versatile catalysts for enantioselective transformations. An alternative to these strategies is the activation of an electrophile or nucleophile by use of a chiral Bronsted acid. Compared to amino-, carbene-, pyridine- and hydrogen-bonding catalyzed transformations, enantioselective Bronsted acid catalysis has only recently emerged as important and promising area of research. In the course of our research program we were able to contribute significantly to the field of enantioselective Bronsted acid catalysis over the last 2 years, and could demonstrate for the first time that in various enantioselective transformations chiral Bronsted acid catalysts can give better or at least comparable results to metal-catalyzed processes. In this chapter we will highlight some of our most recent results and will, additionally, describe how we initially entered the field of asymmetric Bronsted acid catalysis by starting of from a biomimetic approach using nature as a role model.

Original languageEnglish
Title of host publicationORGANOCATALYSIS
EditorsMT Reetz, B List, S Jarcoch, H Weinmann
PublisherSpringer-Verlag Berlin Heidelberg
Pages207-253
Number of pages47
ISBN (Print)978-3-540-73494-9
StatePublished - 2008
Externally publishedYes
EventErnst-Schering-Foundation Symposium on Organocatalysis - Berlin, Germany
Duration: Apr 18 2007Apr 20 2007

Publication series

NameErnst Schering Foundation Symposium Proceedings
PublisherSPRINGER-VERLAG BERLIN
Volume2
ISSN (Print)0947-6075

Conference

ConferenceErnst-Schering-Foundation Symposium on Organocatalysis
CountryGermany
CityBerlin
Period04/18/0704/20/07

Keywords

  • MANNICH-TYPE REACTION
  • DIELS-ALDER REACTION
  • ASYMMETRIC STRECKER REACTION
  • FRIEDEL-CRAFTS REACTION
  • ALPHA-AMINO NITRILES
  • REDUCTIVE AMINATION
  • TRANSFER HYDROGENATION
  • GALIPEA-OFFICINALIS
  • NAZAROV CYCLIZATION
  • REGIOSELECTIVE FUNCTIONALIZATION

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