Smith E,
Jones KD,
O’Brien L,
Argent SP,
Salome C,
Lefebvre Q,
Valery A,
Böcü M,
Newton GN,
Lam HW.
*
University of Nottingham, UK
Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.
J. Am. Chem. Soc. 2023;
145: 16365-16373
DOI:
10.1021/jacs.3c03207
Key words
cubanes - cuneanes - rearrangement - silver catalysis
Significance
Lam and co-workers disclosed a silver(I)-catalyzed rearrangement of 1,4-disubstituted cubanes to 1,3- or 2,6-disubstituted cuneanes. The regioselectivity is strongly dependent on the electronic character of the substituents.
Comment
To explore those strained hydrocarbons as isosteres of 1,3-disubstituted benzenes, an analogue of the anticancer drug sonidegib was prepared by replacing the 1,2,3-trisubstituted benzene with a 1,3-disubstituted cuneane.
