Studies of Memory of Chirality in Amide Radical Cyclizations

Radical cyclization of amide substrates was performed to establish the Memory of Chirality (MOC). Amides with N-tert-butyl substituent due to their hindered rotation around C-N bond gives cyclized product with retention of configuration upon radical reaction condition. Chiral GC analysis and theoretical optical rotation calculation were used to verify the MOC. An unexpected 1,4-phenyl radical migration was also observed during the radical reaction of N-benzyl substituted amides