Stereoselective Substitution in 2-Bromo Amides in the Presence of Ag(1+) or Ag2O
Bromine displacement by a primary, secondary, or tertiary amine, or methanol, in chiral nonracemic (S)-2-bromopropanamides 1 occurs with high yields and stereoselectivity.Soluble Ag(1+) promotes inversion, and solid Ag2O promotes retention of configuratio