An update on the stereoselective synthesis of γ-amino acids

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

“…γ‐Amino acids hold increasing promise for potential applications in therapeutics γ‐peptides and foldamers [208–210] . One example of chiral phosphono‐γ‐amino acid was presented by Smith et al .…”

Visible‐Light‐Mediated Metal‐Free Difunctionalization of Alkenes with CO2 and Silanes or C(sp3)−H Alkanes

“…With the successful development of silacarboxylation of electron‐deficient alkenes, we envisioned that the same strategy might be extended to carbocarboxylation of alkenes using unprefunctionalized C(sp 3 )−H bonds and CO 2 as feedstocks. Alkene difunctionalization by C(sp 3 )‐H activation will significantly enlarge the molecular scaffolds accessible by this visible‐light‐promoted metal‐free protocol, producing for example, γ‐amino acids which are important structural motifs in a myriad of biologically active compounds . As illustrated in Scheme , we found that the carbocarboxylation of alkenes proceeded efficiently under the optimized conditions developed for silacarboxylation.…”

“…Moreover,the silacarboxylation could be extended to other types of electron-deficient alkenes,s uch as acrylate (3m-3o), acrylamide (3p), vinylsulfone (3q), and acrylonitrile (3r), to give products in moderate to good yields.T his mild protocol was applied successfully to late-stage synthetic elaboration of biologically relevant complex molecules (3s, 3t). [19] As illustrated in Scheme 3, we found that the carbocarboxylation of alkenes proceeded efficiently under the optimized conditions developed for silacarboxylation. Tr is(trimethylsilyl)silane appeared to be the most effective silane reagent (3z), perhaps due to the enhanced stability of the supersilyl radical species.T he b-silyl acid products can be easily converted to other silicon containing molecules which can find potential applications in material and pharmaceutical science.…”

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis ofmeso-cyclic anhydrides

“…In the case of mono-substituted cyclic substrates, including alkyl- (Table 2, entries 5–7), ether- (entry 8), aryl-substitution (entries 9–11), moderate enantioselectivities were detected. Moreover, the chiral mono-substituted products are versatile key building blocks for the synthesis of a variety of the industrially important pharmaceuticals, such as γ-aminobutyric acid (GABA) and γ-amino-β-hydroxybutyric acid (GABOB) analogues (baclofen HCl and pregabalin) [51–54], HMG-CoA reductase inhibitors (“statins”) [55–57], etc.…”