Highly enantioselective carbene insertion into N–H bonds of aliphatic amines

Amine antidote for poisoned catalyst

23 March 2020

A combination of two catalysts can overcome a sticky problem in the synthesis of amino acids.

Nitrogen-containing molecules called chiral amines are in strong demand as pharmaceuticals and agrochemicals. Amino acids, the building blocks of proteins, are one major chiral amine family.

Simple structures called aliphatic amines should be ready starting materials for many amino acids, but aliphatic amines stick to the transition-metal catalyst needed to trigger the conversion, poisoning the catalyst and halting the reaction.

Replacing the transition-metal catalyst with two catalysts operating in tandem — a copper catalyst that initiates the conversion and a chiral organocatalyst that completes the task — overcomes this limitation, an all–Nankai University team has shown.

The discovery offers a potential strategy for other reactions in which strongly coordinating ‘sticky’ starting materials poison the catalyst, the researchers consider.

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References

1. Science 366, 990–994 (2019). doi: 10.1126/science.aaw9939