Catalytic Asymmetric Inverse-Electron Demand 1,3-Dipolar Cycloaddition of Isoquinolinium Methylides with Enecarbamates by a Chiral N,N′-Dioxide/Ag(I) Complex

The first catalytic asymmetric inverse-electron demand [3 + 2]-cycloaddition of isoquinolinium methylides with enecarbamates has been realized by using a N,N'-dioxide/Ag(1) complex. The optically active pyrroloisoquinolines and pyrrolophthalazine were obtained in up to 99% yield, >19:1 d.r., and 95% ee. On the basis of fluorescence, ESI-MS analysis, and X-ray structure of the product, a reasonable transition state was proposed.