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.
1995
Dangeli, F; Marchetti, Paolo; Bertolasi, Valerio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1198187
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