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Studies of Memory of Chirality in Amide Radical Cyclizations



Radical cyclizations of amide substrates were 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

Year: 2012
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Provided by: D-Scholarship@Pitt

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