Chiral amines are found ubiquitously in natural products and small molecule pharmaceuticals, and thus they are important targets for the development of new synthetic methodologies. Of the different types of non-racemic amines, propargyl amines are particularly interesting as they can be readily converted to nitrogen-containing heterocycles and utilizing these amines as key synthetic building blocks has been a strategy to rapidly introduce complexity to target structures for many years. In the past few decades, the direct access to chiral secondary propargyl amines has garnered significant interest. Several useful methodologies have been developed to achieve this via imine alkynylation. However, amidst the many advancements, limitations still remain. To further expand access to these important compounds, an enantioselective Cu-catalyzed alkynylation using StackPhos has been developed. Here we present this methodology that utilizes Lewis acid activated iminium ions to access the desired chiral secondary propargyl amines in high selectivity.

Enantioselective synthesis of secondary propargyl amines

ACS Spring 2022

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