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Asymmetric Protonation of Carbanions and Polar Double Bonds: Application to Total Syntheses

Stereoselective Synthesis by Bond Formation

  1. Thomas Poisson1,
  2. Shū Kobayashi2

Published Online: 2 OCT 2013

DOI: 10.1002/9781118596784.ssd031

Stereoselective Synthesis of Drugs and Natural Products

Stereoselective Synthesis of Drugs and Natural Products

How to Cite

Poisson, T. and Kobayashi, S. 2013. Asymmetric Protonation of Carbanions and Polar Double Bonds: Application to Total Syntheses. Stereoselective Synthesis of Drugs and Natural Products. 1–32.

Author Information

  1. 1

    Laboratory COBRA UMR CNRS 6014, IRCOF–INSA de Rouen, St Etienne du Rouvray, France

  2. 2

    Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan

Publication History

  1. Published Online: 2 OCT 2013

Abstract

This chapter covers asymmetric protonation methodologies and their applications to total synthesis of bioactive and natural products. The asymmetric protonation of carbanions, α-stabilized carbanions (metal and silicon enolates), as well as asymmetric protonation of polar double bonds (ketenes and Michael acceptors) are disclosed. A strong emphasis is placed on their synthetic applications toward total synthesis of natural and pharmacologically active products. The aim of this chapter is to summarize what has been done in the field and to highlight the asymmetric protonation as a useful synthetic tool.

Keywords:

  • asymmetric protonation;
  • drug;
  • natural product;
  • synthesis;
  • carbanion;
  • polar double bond;
  • total synthesis;
  • metal enolate;
  • silicon enolate;
  • stereoselective synthesis;
  • C[BOND]H bond formation;
  • ketene;
  • Michael acceptor;
  • decarboxylative protonation;
  • pharmaceutical