Cycloaddition Reactions of Highly Stabilized Isoquinolinium Methylides to Nonactivated Olefins and Electron-Rich Olefins

Article abstract of DOI:10.1246/bcsj.61.2513

Highly stabilized isoquinolinium methylides bearing two electron-withdrawing substituents at the ylide carbon undergo cycloadditions with aryl-substituted olefins (acenaphthylene,(E)- and (Z)-stilbenes, indene, and stirene), alkyl-substituted olefins (norbornene, (Z)-3-hexene-1,6-dinitrile, 1-hexene, 2-propen-1-ol, and 3-(trimethylsilyloxy)propene), and electron-rich olefins (vinylene carbonate, butyl vinyl ether, and phenyl vinyl sulfide).These cycloadditions proceed in an exclusively regioselective and mostly stereoselective manner.