Catalytic enantioselective synthesis of quaternary carbon stereocentres

Nature. 2014 Dec 11;516(7530):181-91. doi: 10.1038/nature14007.

Abstract

Quaternary carbon stereocentres-carbon atoms to which four distinct carbon substituents are attached-are common features of molecules found in nature. However, before recent advances in chemical catalysis, there were few methods of constructing single stereoisomers of this important structural motif. Here we discuss the many catalytic enantioselective reactions developed during the past decade for the synthesis of single stereoisomers of such organic molecules. This progress now makes it possible to incorporate quaternary stereocentres selectively in many organic molecules that are useful in medicine, agriculture and potentially other areas such as flavouring, fragrances and materials.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Agrochemicals / chemical synthesis
  • Agrochemicals / chemistry
  • Alkylation
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Carbon / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic*
  • Cortisone / chemistry
  • Cyclization
  • Metals / chemistry
  • Molecular Structure
  • Morphine / chemistry
  • Organic Chemicals / chemical synthesis*
  • Organic Chemicals / chemistry*
  • Palladium / chemistry
  • Pharmaceutical Preparations / chemical synthesis
  • Pharmaceutical Preparations / chemistry
  • Stereoisomerism
  • Terpenes / chemical synthesis
  • Terpenes / chemistry

Substances

  • Agrochemicals
  • Biological Products
  • Metals
  • Organic Chemicals
  • Pharmaceutical Preparations
  • Terpenes
  • Palladium
  • Carbon
  • Morphine
  • Cortisone