Catalytic asymmetric cationic shifts of aliphatic hydrocarbons

Vijay N. Wakchaure, William DeSnoo, Croix J. Laconsay, Markus Leutzsch, Nobuya Tsuji, Dean J. Tantillo () and Benjamin List ()
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Vijay N. Wakchaure: Max Planck Institut für Kohlenforschung
William DeSnoo: University of California, Davis
Croix J. Laconsay: University of California, Davis
Markus Leutzsch: Max Planck Institut für Kohlenforschung
Nobuya Tsuji: Hokkaido University
Dean J. Tantillo: University of California, Davis
Benjamin List: Max Planck Institut für Kohlenforschung

Nature, 2024, vol. 625, issue 7994, 287-292

Abstract: Abstract Asymmetric catalysis is an advanced area of chemical synthesis, but the handling of abundantly available, purely aliphatic hydrocarbons has proven to be challenging. Typically, heteroatoms or aromatic substructures are required in the substrates and reagents to facilitate an efficient interaction with the chiral catalyst. Confined acids have recently been introduced as tools for homogenous asymmetric catalysis, specifically to enable the processing of small unbiased substrates1. However, asymmetric reactions in which both substrate and product are purely aliphatic hydrocarbons have not previously been catalysed by such super strong and confined acids. We describe here an imidodiphosphorimidate-catalysed asymmetric Wagner–Meerwein shift of aliphatic alkenyl cycloalkanes to cycloalkenes with excellent regio- and enantioselectivity. Despite their long history and high relevance for chemical synthesis and biosynthesis, Wagner–Meerwein reactions utilizing purely aliphatic hydrocarbons, such as those originally reported by Wagner and Meerwein, had previously eluded asymmetric catalysis.

Date: 2024
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DOI: 10.1038/s41586-023-06826-7

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