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A Light Driven Enantioselective Synthesis of Pyrroline Derivatives via Radical/Polar Cascade Reaction.

In the present work, a light-driven, atom-economical strategy that unlocks access to enantioenriched substituted chiral 1-pyrroline derivatives is introduced. The methodology lays in the distal functionalization of acyl heterocycles enabling a hydrogen atom transfer (HAT) and the use of tailored made ketimines as reliable electrophilic partners. This transformation is translated to an enantiocontrolled radical/polar cascade reaction, producing water as sole by-product, where stereocontrol is dictated by coordination to a chiral-at-rhodium catalyst. In the first stage of the reaction, the recently generated prochiral C(sp 3 ) radical interacts with the corresponding ketimine, followed by a polar intramolecular condensation with the remaining carbonyl group, delivering the aforementioned products with high enantioselectivity (up to >99% ee ) and overall good yields.