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. 2020 Dec 21;59(52):23516-23520.
doi: 10.1002/anie.202009892. Epub 2020 Oct 19.

Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2 -Amino Acids

Kai Wang  1 , Jianliang Yu  1 , Ying Shao  1 , Shengbiao Tang  1 , Jiangtao Sun  1
Affiliations

Forming All-Carbon Quaternary Stereocenters by Organocatalytic Aminomethylation: Concise Access to β2,2 -Amino Acids

Kai Wang et al. Angew Chem Int Ed Engl. .

Abstract

The asymmetric synthesis of β2,2 -amino acids remains a formidable challenge in organic synthesis. Here a novel organocatalytic enantioselective aminomethylation of ketenes with stable and readily available N,O-acetals is reported, providing β2,2 -amino esters bearing an all-carbon quaternary stereogenic center in high enantiomeric ratios with a catalytic amount of chiral phosphoric acid. Typically, this transformation probably proceeds through an asymmetric counter-anion-directed catalysis. As a result, a concise, practical, and atom-economic protocol toward rapidly access to β2,2 -amino acids has been developed.

Keywords: N,O-acetals; amino acids; ketenes; organocatalysis; phosphoric acid.

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References

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