Questions/Amines/If the migrating gro...
Preparation of AminesAmines

If the migrating group 'R' in the starting amide ( RCONH2R-CONH_2 ) is chiral, what is the stereochemical outcome regarding that chiral center in the product amine?

Expert Answer

The reaction proceeds with Retention of Configuration at the chiral center of the migrating group R. The migration step is intramolecular and concerted; the bond from C to R breaks simultaneously as the N to R bond forms, so the stereocenter does not invert.

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