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Biomimetic Organocatalytic C–C-Bond Formations

  • D. Enders
  • M. R. M. Hüttl
  • O. Niemeier
Conference paper
Part of the Ernst Schering Foundation Symposium Proceedings book series (SCHERING FOUND, volume 2007/2)

Abstract

Mother Nature utilizes simple precursors to build up complex organic molecules efficiently. One important example is the C3 building block dihydroxyacetone phosphate, which is used in various enzyme-catalyzed reactions. Following this biosynthetic strategy the DHAP equivalent ‘dioxanone’ can be used in organocatalytic reactions to synthesize sugars, aminosugars, carbasugars, polyoxamic acids and sphingosines. In this respect, organocatalytic domino reactions can also be seen as biomimetic as they are reminiscent of tandem reactions that may occur during biosyntheses of complex natural products. In nature, the coenzyme thiamin (vitamin B1), a natural thiazolium salt, is used in biochemical nucleophilic acylations (‘Umpolung’). The catalytic active species is a nucleophilic carbene. Mimicking this approach, organocatalytic carbene catalysis has emerged to an exceptionally fruitful research area, which is used in asymmetric C–C bond formations.

Keywords

Enantiomeric Excess Reductive Amination Mannich Reaction Aldol Reaction Aldol Product 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Authors and Affiliations

  1. 1.Institute of Organic ChemistryRWTH Aachen UniversityAachenGermany

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