1437787-97-7

Upstream product

• 932-87-6 1-Bromo-2-phenylacetylene 
• 286376-23-6 4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide 

Downstream Products

• 1437788-13-0 4-acetyl-3-phenyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one 
• 1437788-23-2 3-phenyl-1-tosyl-4-vinyl-1,5-dihydro-2H-pyrrol-2-one 

Relevant academic research and scientific papers

Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles

The generation of metal carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. However, most of these transformations are based on the use of noble-metal catalysts and successful examples of such an asymmetric version are still very scarce. Here a copper-catalyzed enantioselective cascade cyclization of N-propargyl ynamides is reported, enabling the practical and atom-economical construction of diverse chiral polycyclic pyrroles in generally good to excellent yields with wide substrate scope and excellent enantioselectivities (up to 97:3 e.r.). Importantly, this protocol represents the first copper-catalyzed asymmetric diyne cyclization. Moreover, mechanistic studies revealed that the generation of donor/donor copper carbenes is presumably involved in this 1,5-diyne cyclization, which is distinctively different from the related gold catalysis, and thus it constitutes a novel way for the generation of donor/donor metal carbenes.

Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes

Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.