Synthesis and optical resolution of 4,5-diaminohomoadamantane: a promising scaffold for chiral ligands and bioactive compounds

• Polina A. Man’kova,
• Vadim A. Shiryaev,
• Olga S. Podlipnova,
• Marat M. Khisyamov,
• Dmitry S. Nikerov,
• Alexander N. Reznikov and
• Yuri N. Klimochkin

Beilstein J. Org. Chem. 2026, 22, 1013–1022, doi:10.3762/bjoc.22.80

• suggest that further molecular design of homoadamantane-based chiral N,N-ligands is promising. Keywords: asymmetric Henry reaction; asymmetric Michael reaction; diaminohomoadamantane; enantiodivergent effect; resolution of racemate; Introduction The chemistry of organic polycyclic cage compounds has

• configurations when using ligands of similar structure indicates an enantiodivergent effect [105]. The ligand 19′ was studied in a model Michael reaction. The reaction of nitrostyrene with diethyl malonate was conducted in chloroform in the presence of ligand 19′, NiBr2, and NEt3 (2 mol % each). This reaction

• -diaminohomoadamantane were obtained. Catalytic systems based on them have been studied in the asymmetric Michael and Henry reactions. Low enantioselectivity (up to 60% ee) was observed, but an enantiodivergent effect was noted in the Henry reaction. Examples of bioactive homoadamantanes. Examples of cage vicinal