Introduction:  Atropisomers are key intermediates in the synthesis of high value P-containing ligands (BINAP, QUINAP etc). Typically enantiopure atropisomeric ligands are synthesised by classical resolution which is wasteful and has to be re-optimised for every new ligand. New methodology to synthesise these compounds would be extremely valuable. Previous work in the group has shown that enantiopure biaryl ether atropisomers can be synthesised by enzymatic desymmetrisation.Discussion:   This methodology has been extended to a series of biaryls; a class of compounds of greater value than the biaryl ethers previously described due to their use as precursors to chiral ligands. It has been found that symmetrical biaryl diols 1  or dialdehydes 2  can be enzymatically desymmetrised by two complimentary methods to give enantiopure 3 . Galactose oxidase M3-5 (GOase) can be employed to oxidise one of the enantiotopic hydroxyl groups of compound 1  to give 3 . Alternatively dialdehyde 2  can be desymmetrised by selective reduction of one formyl group using a ketoreductase (KRED) to give enantiopure 3 . This work offers a sustainable, greener alternative to the current methods employed to produce atropisomers. 

Biocatalytic production of biaryl atropisomers

248th National Meeting (2014)

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