Synthesis of γ-Amino Acid Esters by 1,4-Addition of Deprotonated α-Aminonitriles and α-(Alkylideneamino)nitriles to α,β-Unsaturated Esters

Abstract

Synthesis of g-Amino Acid Esters by 1,4-Addition of Deprotonated a-Aminonitriles and a-(Alkylideneamino)nitriles to a,b-Unsaturated Esters g -A m i n o A c i d E s t e r s f r o m a -A m i n o n i t r i l e sAbstract: a-Aminonitriles and a-(alkylideneamino)nitriles can serve as readily available a-aminocarbanion equivalents. Their conjugate addition to a,b-unsaturated esters followed by reduction furnishes polysubstituted g-amino acid esters in moderate to high yield.

Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones

“…for the construction of γ-amino acids [32], pyrrolidines [33], as well as pyrroles [34–35]. If an additional conjugated double bond is present, the anions of α-(alkylideneamino)nitriles 3 can undergo an electrocyclic ring closure to furnish 3,4-dihydro-2 H -pyrrole-2-carbonitriles 6 after reprotonation [36].…”