63183-18-6Relevant academic research and scientific papers
Synthesis of non-racemic dihydrofurans via Ni(II)-catalyzed asymmetric Michael addition
Nikerov, Dmitry S.,Ashatkina, Maria A.,Shiryaev, Vadim A.,Tkachenko, Ilya M.,Rybakov, Victor B.,Reznikov, Alexander N.,Klimochkin, Yuri N.
, (2021)
A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed. Addition of carbonyl compounds which contain bulky adamantyl substituent and β-keto or phosphonate group to conjugated α-bromonitroolefins in the presence of a chiral Ni(II) complex gave corresponding non-racemic products of Michael reaction. These adducts were used for intramolecular cyclization leading to trans-4,5-dihydrofurans with two stereocenters. Resulting trans-4,5-dihydrofurans were obtained in good yields with moderate to high enantioselectivities (84–99% ee) and excellent diastereoselectivities (dr >99%).
