A powerful cascade reaction process for the construction of functionalized cis-bicyclo [3.3. 0] octenes has been developed. Carbolithiation of 3-methylene-1, 4-cyclooctadiene with 1°, 2°, or 3° alkyllithium reagents leads to cyclooctadienyl anions, which undergo disrotatory electrocyclization and subsequent trapping with carbon, oxygen, sulfur, or silicon electrophiles to provide functionalized cis-bicyclo [3.3. 0] octenes. Transmetalation of the ...
