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Updated: Oct 5, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
One Soai reaction, two mechanisms?
1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands. y.geiger@rug.nl.
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.
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