Challenging mirror molecules made with stereochemistry destroying reaction

By Katrina Krämer2018-04-26T14:29:00

Computational image of the squaramide catalyst (bottom) holding the carbocation intermediate (top) in the chirality-inducing step. Non-covalent bonds such as charge interactions and aromatic stacking allow the nucleophile to only attach to one side of the

Source: © Nature/Macmillan

Clever catalyst repurposes classic nucleophilic substitution to make chiral quaternary carbon centres

A substitution reaction known for destroying stereochemistry has been converted into a chirality-creating reaction to tackle one of the toughest organic chemistry challenges: making quaternary carbon centres.

There is currently no perfect way to make quaternary stereocentres. Most methods rely on using a pro-chiral substrate – a compound like a tri-substituted alkene with well-defined stereochemistry. But making these pro-chiral substrates is a challenge in itself.