- Intramolecular functional group differentiation as a strategy for the synthesis of bridged bicyclic β-amino acids
Differentiation of identical electrophilic functional groups (carboxylates) by a strategically placed internal nucleophile (an amino group) in cyclic precursors was used as a key general approach to functionalized azabicyclic scaffolds. The utility of the method was demonstrated by the synthesis of three bicyclic β-amino acids (analogues of nipecotic acid), which were prepared in good yields and on a relatively large scale.
- Tymtsunik, Andriy V.,Kokhan, Serhii O.,Ivon, Yevhen M.,Komarov, Igor V.,Grygorenko, Oleksandr O.
p. 22737 - 22748
(2016/03/26)
- Gram-scale synthesis of 3,5-methanonipecotic acid, a nonchiral bicyclic β-amino acid
A scalable synthesis was developed of 3,5-methanoni?pecotic acid (3-azabicyclo[3.1.1]heptane-1-carboxylic acid), a rare example of a conformationally constrained nonchiral β-amino acid, potentially useful in peptide engineering and peptidomimetic drug design. A retrosynthetic strategy based on disconnections exclusively within the symmetry planes of the target and the intermediate molecules was found to be useful and might deliver expedite syntheses in other similar cases. Georg Thieme Verlag Stuttgart New York.
- Tymtsunik, Andriy V.,Bilenko, Vitaliy A.,Grygorenko, Oleksandr O.,Komarov, Igor V.
