Aug 2026· Advancement of science· 0 citations· 55 references
Medicine
Abstract
ABSTRACT Chiral alkyl selenides are valuable motifs in medicinal chemistry and redox‐active molecular design, yet enantioselective hydroselenylation of unactivated alkenes remains challenging due to limited control over regio‐ and enantioselectivity. Here, we report nickel‐hydride‐catalyzed enantio‐ and regioselective hydroselenylation of unactivated alkenes directed by native amide groups using readily available diselenides. The method accommodates both terminal and internal alkenes as well as both aryl and alkyl diselenides, exhibiting broad functional‐group tolerance and delivering structurally diverse chiral aliphatic selenides with high regio‐ and enantioselectivity under mild conditions. Mechanistic studies support enantiodetermining hydronickelation followed by single‐electron diselenide activation and selective capture of the selenium radical by the chiral alkyl–nickel intermediate. This work establishes a general platform for asymmetric C─Se bond formation through the integration of NiH catalysis and radical selenium transfer.
ABSTRACT β‐Chiral phenethyl alcohols represent a privileged scaffold in bioactive molecules, chemical probes, and functional materials, serving as versatile synthons in organic synthesis. Herein, we report the first Ni/photoredox‐catalyzed stereoconvergent C(sp3)−C(sp2) cross‐electrophile coupling of racemic epoxides w...
Hongyan Lan, Sheng-Zhou Jin, Zhao-Dong Xu et al.· Advancement of science· 0 citations
Enantioselective meta-C─H functionalization of pyridines represents a long-standing challenge that, if resolved, would open transformative avenues in synthesis and drug discovery. Radical-based approaches are particularly attractive yet have remained elusive. We here report a radical enantioconvergent meta-C─H alkylati...
Shi Qin, Xin-Yu Gao, Qi-Xin Li et al.· Science Advances· 0 citations
ABSTRACT Chiral spirocyclopropyl heterocycles have emerged as privileged three‐dimensional structural motifs in medicinal chemistry. Nevertheless, efficient catalytic enantioselective assembly of such compounds still faces considerable synthetic difficulties. Herein, we describe a rhodium‐mediated asymmetric [2+1] cycl...
Yuanhao Zhu, Youzhi Xu, Weitao Zhang et al.· Advancement of science· 1 citation
The enantioselective C–H functionalization of benzylamines using earth-abundant metal catalysts remains a formidable challenge due to conformational flexibility and long-range chiral induction. Herein, we describe a Ni(II)-catalyzed enantioselective C–H alkynylation of benzylamines using a removable picolinamide dire...
Metal-catalyzed enantioselective construction of C(sp 3 )–O bonds from racemic alkyl electrophiles has attracted considerable attention, yet existing approaches typically proceed through organometallic or radical intermediates. Here, we highlight a halide-enabled dynamic kinetic resolution platform that integrates rapi...
Jin-Ze Du, Xin-Yi Zhang, Yu-Li He· Synlett : Accounts and Rapid...· 0 citations
The development of general methods for the enantioselective synthesis of axially chiral molecules remains a longstanding challenge in organic synthesis. Among these, allenes represent a particularly important class of motifs due to their unique structural and electronic properties, yet their catalytic enantioselective...
