Xiaofeng Tong

Pd(0)-Catalyzed Iodoalkynation of Norbornene Scaffolds: The Remarkable Solvent Effect on Reaction Pathway

A palladium-catalyzed iodoalkynation of norbornene has been realized with the use of alkynyl iodides 1, which is found to be strongly solvent-dependent. MeCN favors 1,7-iodoalkylation product 3 while CCl(4) leads to 1,2-iodoalkylation product 4.

Palladium-catalyzed Heck-type reaction of oxime ether bearing a pendant vinyl iodide moiety

A Pd(0)-catalyzed intramolecular Heck-type reaction of oxime ether has been developed, providing convenient access to heterocyclic oximes.

Phosphine-Catalyzed Asymmetric (3 + 2) Annulations of δ-Acetoxy Allenoates with β-Carbonyl Amides: Enantioselective Synthesis of Spirocyclic β-Keto γ-Lactams

While the phosphine catalysis is a powerful tool for the construction of N-heterocycles, the phosphine-catalyzed annulations toward lactam motif are still extremely scarce. Here, we report the asymmetric (3 + 2) annulations of δ-acetoxy allenoates with β-carbonyl amides by using the (R)-SITCP catalyst. The δC and γC of allenoate respectively engage in annulation with the αC and N of the amide, forging a γ-lactam with good to excellent stereoselectivity.

Phosphine-Catalyzed (3 + 2) Annulation of δ-Acetoxy Allenoates with 2-Sulfonamidomalonate: Synthesis of Highly Substituted 3-Pyrrolines and Mechanistic Insight

A mild and efficient synthetic protocol for 3-pyrrolines via the phosphine-catalyzed (3 + 2) annulation of δ-acetoxy allenoates with 2-sulfonamidomalonate is reported. The asymmetric version (up to 83% ee) is also achieved by using phosphine ( R)-SITCP as the catalyst. Mechanistic experiments disclose that the involved deprotonation of amide N-H and aza-addition to vinyl phosphonium might proceed in a concerted manner.