Repozytorium
Wyszukaj
Kolekcje
Inne
The most twisted acyclic amides: structures and reactivity.
Autorzy
Rok wydania
2018
Czasopismo
Numer woluminu
20
Strony
7771-7774
DOI
10.1021/acs.orglett.8b03175
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The synthesis, crystal structures, and reactivity of the most twisted acyclic amides described to date are reported. Substitution at the nitrogen atom in simple benzamides with Ts and acyl or carbamate groups provides a unique way to achieve almost perpendicular twist in N-acyclic amides (τ = 77°, N = Ac; τ = 87°, N = Boc). The overlap between the Nlp and CO π* orbital is disrupted due to geometrical constraints around the N-substituents. The perpendicular acyclic twisted amides represent a transition state mimic of cis–trans peptide isomerization thus far only accessible by excessively twisted bridged lactams.
Adres publiczny
http://doi.org/10.1021/acs.orglett.8b03175
Strona internetowa wydawcy
Podobne publikacje
Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N−C(X) Resonance
Zhao Qun, Li Guangchen, Nareddy Pradeep, Jordan Frank, Lalancette Roger, Szostak Roman, Szostak Michal
Acyl and decarbonylative Suzuki coupling of N-acetyl amides: electronic tuning of twisted, acyclic amides in catalytic carbon–nitrogen bond cleavage.
Liu Chengwei, Li Guangchen, Shi Shicheng, Meng Guangrong, Lalancette Roger, Szostak Roman, Szostak Michal
Electrophilicity scale of activated amides: 17O NMR and 15N NMR chemical shifts of acyclic twisted amides in N−C(O) cross‐coupling.
Ielo Laura, Pace Vittorio, Holzer Wolfgang, Rahman Md. Mahbubur, Meng Guangrong, Szostak Roman, Szostak Michal