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Inversion of Chirality - Just by Changing the Metal!

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27 December 2004

An interesting phenomenon, described by the authors* as “elective” enantioselectivity, has been observed in the enantioselective fluorination of indanone carboxylates using the Box-Ph chiral ligand. Using the same chiral ligand (same antipode), but switching the metal catalyst from copper to nickel gave a complete reversal of enantioselectivity as summarised in the scheme:

Worth considering broadening the range metal components next time you screen for an asymmetric transformation.

* N. Shibata et al., SYNLETT, 2004, (10), 1703-1706