10. Brønsted Acids

  1. Peter I. Dalko
  1. Yunus E. Türkmen,
  2. Ye Zhu and
  3. Viresh H. Rawal

Published Online: 23 AUG 2013

DOI: 10.1002/9783527658862.ch10

Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications

Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications

How to Cite

Türkmen, Y. E., Zhu, Y. and Rawal, V. H. (2013) Brønsted Acids, in Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications (ed P. I. Dalko), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527658862.ch10

Editor Information

  1. Université Paris-Descartes, PRES Sorbonne Paris Cité, CNRS, 45, rue des Saints-Pères, 75270 Paris Cedex 06, France

Publication History

  1. Published Online: 23 AUG 2013
  2. Published Print: 23 OCT 2013

ISBN Information

Print ISBN: 9783527332366

Online ISBN: 9783527658862

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Keywords:

  • hydrogen bonding catalysis;
  • Brønsted acids;
  • enantioselective catalysis;
  • taddols;
  • chiral squaramides;
  • guanidines

Summary

Enantioselective catalysis by chiral hydrogen-bond donors and Brønsted acids has emerged as one of the most significant new advances in organic chemistry over the past two decades. This enabling technology is an important portion of the rapidly developing field of metal-free asymmetric catalysis, commonly described as organocatalysis. This chapter reviews the major types of hydrogen-bonding catalysts with their historical backgrounds as well as recent developments in their synthesis and applications. It commences with a brief introduction to the concept of hydrogen bonding and then delves into a discussion of several catalyst subclasses, including alcohols, squaramides, guanidines/guanidiniums, aminopyridiniums, tetraaminophosphoniums, and axially chiral dicarboxylic acids.