The presence of nitrogen within bioactive molecules is a hallmark structural feature, and with the push to explore greater three-dimensional space in drug discovery, the instances of nitrogen-substituted stereogenic centers is becoming steadily more desirable. The development of new catalytic methods, particularly stereoselective protocols, for accessing these chiral amines are therefore highly sought after. Some amine scaffolds, however, are challenging to prepare through normal carbon–carbon bond-forming methods. We have developed 2-azadienes as enamine umpolung reagents for the catalytic synthesis of several amine-containing motifs, including vicinal amino alcohols and diamines. Transformations furnish an array of aliphatic amines with excellent chemo-, diastereo-, and enantioselectivity.

New reagents and catalytic strategies for the umpolung synthesis of chiral amines

ACS Spring Meeting 2021

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