Light-Driven Enantioselective Synthesis of Pyrroline Derivatives by a Radical/Polar Cascade Reaction

Herein, a light-driven, atom-economical process that provides access to enantiomerically enriched substituted chiral 1-pyrroline derivatives is introduced. The strategy involves the distal functionalization of acyl heterocycles through a hydrogen-atom transfer (HAT) process and the use of tailor-made ketimines as reliable electrophilic partners. This transformation is translated into an enantiomerically controlled radical/polar cascade reaction in which water is produced as the sole by-product and stereoselectivity is dictated by coordination to a chiral-at-rhodium catalyst.

Automated summary

This study introduces a light-driven, atom-economical process for synthesizing enantiomerically enriched substituted chiral 1-pyrroline derivatives through distal functionalization of acyl heterocycles and the use of tailor-made ketimines as partners. Water is the sole by-product of the reaction, and stereoselectivity is controlled by coordination to a chiral-at-rhodium catalyst.