Chiral Lewis Acid-Catalyzed Intramolecular [2 + 2] Photocycloaddition: Enantioselective Synthesis of Azaarene-Functionalized Azabicyclo[2.1.1]hexanes and Bicyclo[1.1.1]pentanes

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 2, 2025

We present an asymmetric intramolecular [2 + 2] photocycloaddition reaction enabled by a dual catalyst system involving DPZ as photosensitizer and chiral Sc(III) complex, leading to azaarene-functionalized 2-azabicyclo[2.2.1]hexanes (aza-BCHs). The approach efficiently preventing racemization during subsequent nitrogen-deletion skeletal editing of aza-BCHs yield 2-substituted bicyclo[1.1.1]pentanes (BCPs). method achieves high ee broad substrate scope, including the successful formation all-carbon quaternary stereocenters. Furthermore, activation simple azaarene substrates Lewis acids in photocatalysis highlights notable contribution this field.

Язык: Английский

Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series trifluoromethyl sulfonates were synthesized via visible-light-induced radical reaction sodium sulfinates and to obtain protons from solvent. dithiosulfonated derivatives bifunctionalization dithiosulfonates.This strategy has advantages mild conditions, good substrate universality high yield up 99% yield.

Язык: Английский