One Soai reaction, two mechanisms?

Chem Soc Rev. 2022 Feb 21;51(4):1206-1211. doi: 10.1039/d1cs01038g.

Abstract

For over 25 years the chemistry community has puzzled over the mechanism of the Soai reaction, a fascinating chemical process which achieves chiral symmetry breaking by combining autocatalysis with asymmetric amplification. In 2020, the groups of Denmark and Trapp each made a proposal, based on extensive experimental work, on what is the catalytic species there: either a tetrameric product alkoxide aggregate ("SMS tetramer") or a product-substrate dimer ("hemiacetal"). These models seemingly oppose and exclude each other; however, they might also be both valid since the studies were conducted on different substrates which are not necessarily equivalent. This is shown in this Viewpoint by an in-depth comparison of the two studies and of data from earlier reports, which opens up to a discussion on this scenario's far-reaching implications on the fundamental understanding of asymmetry-amplifying autocatalysis.

Publication types

  • Review

MeSH terms

  • Catalysis
  • Polymers*
  • Stereoisomerism

Substances

  • Polymers