Metal-Catalyzed Asymmetric Michael Addition in Natural Product Synthesis

Chemistry. 2017 Mar 23;23(17):4023-4036. doi: 10.1002/chem.201604110. Epub 2016 Dec 19.

Abstract

Asymmetric catalysis for chiral compound synthesis is a rapidly growing field in modern organic chemistry. Asymmetric catalytic processes have been indispensable for the synthesis of enantioselective materials to meet demands from various fields. Michael addition has been used extensively for the construction of C-C bonds under mild conditions. With the discovery and development of organo- and metal-catalyzed asymmetric Michael additions, the synthesis of enantioselective and/or diastereoselective Michael adducts has become possible and increasingly prevalent in the literature. In particular, metal-catalyzed asymmetric Michael addition has been employed as a key reaction in natural product synthesis for the construction of contiguous quaternary stereogenic center(s), which is still a difficult task in organic synthesis. Previously reported applications of metal-catalyzed asymmetric Michael additions in natural product synthesis are presented here and discussed in depth.

Keywords: asymmetric Michael addition; metal catalysis; natural product; total synthesis.

Publication types

  • Review

MeSH terms

  • Biological Products / chemical synthesis*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Metals / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Biological Products
  • Metals