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Updated: Jul 10, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Enantioselective Multifunctionalization with Rh Carbynoids
Yu Qian1, Jie Tang1, Xiaoyu Zhou2
1Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China.
Abstract:
Multifunctionalization from the interception of active intermediates is an attractive synthetic strategy for the efficient construction of complex molecular scaffolds in an atom and step economic fashion. However, the design of reactions involving metal carbynoids that exhibit carbene/carbocation behavior is currently limited, and developing catalyst-controlled highly enantioselective versions poses significant challenges. In this study, we present the first asymmetric trifunctionalization reactions with rhodium carbynoids. This reaction unveils the distinctive reactivity of the carbynoid precursor, enabling it to react with simultaneously two nucleophiles and one electrophile. This process involves the formation of two distinct carbene ylides with the alcohol/carbamate and the trapping of one ylide with the imine, resulting in the formation of three new bonds. Furthermore, this strategy allows for the divergent synthesis of a wide array of β-amino esters in high yields and exceptional enantioselectivity.
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