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Tricyclo[5.2.1.0^1,5]decanes are often found in bioactive natural products; however, their synthesis poses significant challenges. Here, the authors report a nickel-catalyzed asymmetric domino cyclization of enynones, providing a rapid and modular synthesis of bridged tricyclo[5.2.1.0^1,5]decane skeletons.

Asymmetric versions of radical-mediated alkene difunctionalizations featuring hydrocarbon precursors are currently elusive. Here the authors report an asymmetric vicinal alkene dicarbofunctionalization based on the activation of C(sp³)–H bonds through the combination of photocatalysed hydrogen atom transfer and nickel catalysis.

The enantioselective C(sp³)–H alkylation of saturated hydrocarbons to construct C(sp³)–C(sp³) bonds is challenging. Now a nickel-catalysed enantioselective C(sp³)–H alkylation of saturated heterocycles using olefins has been developed. The enantio- and diastereoselective C(sp³)–H alkylation of saturated hydrocarbons with alkenyl boronates has also been achieved to give alkyl boronates containing 1,2-adjacent C(sp³) stereocentres.

Catalytic asymmetric synthesis of optically pure 1,n-diols from bulk chemicals in a stereoselective and atom-economical manner remains a challenge. Here, the authors report a modular method for the synthesis of enantioenriched 1,2-diols and 1,3-diols from the high-production-volume chemicals ethylene glycol and 1,3-propanediol, respectively.

The synthesis of C-glycosides relies on specially designed glycosyl donors, which are often unstable and require multi-step synthesis. Now a facile method for the synthesis of diverse C-glycosides from readily available and stable 1-deoxyglycosides has been developed. A ligand-controlled site-divergent functionalization of carbohydrates by C–H sampling/nickel-catalysed cross-coupling has also been realized.

Divergent functionalizations of pi bonds allow for synthetic chemists to move from simplicity to complexity. Here, the authors report a nickel-catalyzed switchable arylation/cyclization of 1,6-enynes in which the nature of the ligand dictates the regioselectivity of alkyne arylation, while the electrophilic trapping reagents determine the selectivity of the cyclization mode.

Transition metal-catalyzed asymmetric cyclization of 1,6-enynes is a powerful tool for the construction of chiral nitrogen-containing heterocycles, but limiting to the use of aryl or alkenyl metal reagents. Here, the authors report Ni-catalyzed enantioselective anti-arylative cyclization and enantiospecific cis-alkylative cyclization of 1,6-enynes.