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An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks

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  • Kirsty Adams
  • Anthony K. Ball
  • James Birkett
  • Lee Brown
  • Ben Chappell
  • Duncan M. Gill
  • P. K.Tony Lo
  • Nathan J. Patmore
  • Craig R. Rice
  • James Ryan
  • Piotr Raubo
  • Joseph B. Sweeney
<mark>Journal publication date</mark>1/04/2017
<mark>Journal</mark>Nature Chemistry
Issue number4
Number of pages6
Pages (from-to)396-401
Publication StatusPublished
Early online date12/12/16
<mark>Original language</mark>English


Heterocyclic architectures offer powerful creative possibilities to a range of chemistry end-users. This is particularly true of heterocycles containing a high proportion of sp3 -carbon atoms, which confer precise spatial definition upon chemical probes, drug substances, chiral monomers and the like. Nonetheless, simple catalytic routes to new heterocyclic cores are infrequently reported, and methods making use of biomass-accessible starting materials are also rare. Here, we demonstrate a new method allowing rapid entry to spirocyclic bis-heterocycles, in which inexpensive iron(III) catalysts mediate a highly stereoselective C-C bond-forming cyclization cascade reaction using (2-halo)aryl ethers and amines constructed using feedstock chemicals readily available from plant sources. Fe(acac) 3 mediates the deiodinative cyclization of (2-halo)aryloxy furfuranyl ethers, followed by capture of the intermediate metal species by Grignard reagents, to deliver spirocycles containing two asymmetric centres. The reactions offer potential entry to key structural motifs present in bioactive natural products.