A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

One-Pot Synthesis of Pyrrolidine-2-ones from Erythruronolactone and Amine

“…For the products 7a-p, the signal for the H 5 proton of the pyrrolidine cycle is around 4.10 ppm to 4.75 ppm and with coupling constant values (J 5,4 = 4.40-6.08 Hz), while the compounds 7a -p showed the chemical shift pattern for single proton H 5 of the pyrrolidine cycle around 4.16 ppm to 4.69 ppm and coupling constant values (J 5,4 trans = 0 Hz). These results are confirmed by the results of Zhou et al [17] in determining the stereochemistry of γ-lactams derivatives.…”

“…The nitrogen introduction often involves azide substitution [15] or oximation [16]. Heavy-metal catalysis was also widely used to install ring systems or hydroxyl groups [17].…”

Design and synthesis of a novel glycosphingolipid derived from polyhydroxy 2-pyrrolidinone and phytoceramide appended by a 1,​2,​3-​triazole linker

“…The trans coupling constants observed for 2-pyrrolidinone 7 (J 3-4, 4-5 = 6 Hz) was in agreement with the literature (Overkleeft et al, 1994, Zhou et al, 2007. Key NOESY cross peaks were observed between H-3 at δ H 4.22 (d, J = 6 Hz) and H-5 at δ H 3.51 (app t, J = 6 Hz) (see Supplementary material); indicating the presence of these two protons on the same side ( Fig 3).…”

Recent Developments in the Synthesis of Pyrrolidine‐Containing Iminosugars

“…[122] In Hanessian's work, two unnatural polyhydroxylated indolizidines were synthesised via methodology that included the BF 3 ·OEt 2 mediated addition of 2-(trimethylsilyloxy)furan to iminium salts, [118] while Yoda and co-workers used a Grignard addition to a lactam en route to the first total syntheses of the pyrrolizidine tetrols hyacinthacine B 1 (245) and hyacinthacine B 2 (246) (Scheme 44). [119] Here lactam 242 [itself prepared form commercially available (S)-(-)-2-pyrrolidine-5-carboxylic acid] was treated with butenylmagnesium bromide to give a ketone that was diastereoselectively reduced using excess NaBH 4 in the presence of CeCl 3 in dilute EtOH solution (0.005 ) to yield alcohol 243.…”