Sep 2026· Journal of the American Chemical Society· Vol 148, pp. 40428 - 40437· 0 citations· 80 references
Abstract
Enantioselective carboamination of allenes especially in conjunction with 3D-metal catalysis remains a significant challenge. We report chiral cyclopentadienyl cobaltIII-catalyzed regio-, chemo-, and enantioselective intermolecular C–H carboamination of racemic allenyl esters with N-phenoxyisobutyramides. The protocol offers an efficient approach for highly selective carboamination of allenes and affords synthetically valuable chiral γ-substituted-β-enamido esters with exceptional selectivities (up to 88% yield, >99:1 er, and >20:1 E/Z). Operating by a kinetic resolution pathway, the transformation was additionally optimized for recovery of enantioenriched allenes with high selectivity factors of up to 138. The utility was showcased by the resolution of methyl-(R,E)-(−)-tetradeca-2,4,5-trienoate, the male bean weevil pheromone.
Catalytic asymmetric approaches to enantioenriched organogermanium compounds remain severely underdeveloped. Herein, we report a CuOAc-catalyzed enantioselective hydrogermylation of 3,3-disubstituted cyclopropenes, which furnishes structurally diverse chiral organogermanes in high to excellent diastereo- and enantiosel...
Jia-Heng Li, Q. Ru, Hu Tian et al.· Angewandte Chemie· 0 citations
A highly regio- and enantioselective synthesis of chiral 3-allyl-1H-indenes has been developed using a Rh(I)/bisoxazolinephosphine catalyst in combination with 4-dimethylaminopyridine (DMAP). The tridentate NPN* ligand binds tightly to Rh(I), effectively preventing catalyst deactivation by the indene products and ena...
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
Enantioselective olefin carboamination is the simultaneous formation of C-N and C-C bonds across an alkene. This method represents a powerful strategy to build molecular complexity with up to two vicinal stereocenters in a single operation. Over the past two decades, transition metal catalyzed enantioselective olefin c...
Zhi-Kun Zhang, V. Sankar, Haichao Shen et al.· Chemical Society Reviews· 0 citations
Chiral arylvinyl-substituted 3-hydroxy-5-oxo esters are valuable motifs in pharmaceuticals, yet their enantiocontrolled synthesis remains challenging. Herein, we report a biocatalytic system using ketoreductases (KREDs) for the highly C3-selective reduction of arylvinyl-substituted 3,5-dicarbonyl esters. Through semira...
Xiao-Qiu Wu, Ming-Yu Zhang, Ming-Yang Yao et al.· Organic Letters· 0 citations
A stereoselective methodology for the synthesis of highly substituted spiropyrrolidines via synergistic catalysis was developed. The transformation is based on a cooperative catalytic system combining chiral phosphoric acid (CPA) catalysis with achiral palladium catalysis and proceeds through a formal [3+2] cycloadditi...
Michael Franc, Ivana Císařová, J. Veselý· Journal of Organic Chemistry· 0 citations
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