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+ promotes inversion, and solid AgzO promotes retention of configuration. However, in the case of Et3N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbutanamid5e, the displacement by a primary or secondary amine or methanol occurs only in the presence of Ag20, possibly with retention of configuration.
STEREOSELECTIVE SUBSTITUTION IN 2-BROMO AMIDES IN THE PRESENCE OF AG+ OR AG2O
MARCHETTI, Paolo;BERTOLASI, Valerio
1995
Abstract
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+ promotes inversion, and solid AgzO promotes retention of configuration. However, in the case of Et3N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbutanamid5e, the displacement by a primary or secondary amine or methanol occurs only in the presence of Ag20, possibly with retention of configuration.File in questo prodotto:
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