Synthesis and absolute configuration of 3‐ethyl and 3‐n‐propylpyrrolidine

Abstract

Optically active 3‐ethyl and 3‐n‐propylpyrrolidine were prepared by two independent routes from their corresponding succinic acids and the absolute configurations were assigned. Maximum optical rotation was also established through evaluation of the degree of racemization of the products obtained via both synthetic routes.

Enantioselective synthesis of 2-substituted 4-aminobutanoic acid (GABA) analogues via cyanomethylation of chiral enolates

“…9, which was considered to be (4S,5R,2'S)-3-(2-cyanomethylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one 7a.…”

Chemoenzymatic Synthesis of Glutamic Acid Analogues: Substrate Specificity and Synthetic Applications of Branched Chain Aminotransferase from Escherichia coli

“…The (2 S ,3 R )-configuration of 2p was demonstrated by oxidative decarboxylation of the residual unreacted ketoacid 1p after the BCAT catalyzed transamination. The known ( S )-2-propylsuccinic acid 9 was identified, thus showing that BCAT displays a high enantioselectivity toward ( R )- 1p .…”

New nitrogen-containing bromophenols from the marine red alga Rhodomela confervoides and their radical scavenging activity

“…Based on these data, the structure of 1 was determined as 3-(2,3-dibromo-4,5-dihydroxybenzyl)pyrrolidine-2,5-dione. The absolute configuration at C-3 was tentatively assigned as S based on the sign of its specific rotation ½a 25 D þ 17 ( C 0.1, MeOH) in comparison with the values reported for the structurally related synthetic compounds S-(+)-2-ethylsuccinimide ([a] D + 1.2, C 0.2, MeOH) and S-(+)-2-n-propylsuccinimide ([a] D + 3.0, C 0.1, MeOH) (Bettoni, Cellucci, & Berardi, 1980).…”