jo8b02601_si_001.pdf (15.45 MB)
Asymmetric Michael Addition of 2‑Acetyl Azaarenes to β‑CF3‑β-(3-indolyl)nitroalkenes Catalyzed by a Cobalt(II)/(imidazoline-oxazoline) Complex
journal contribution
posted on 2018-12-13, 00:00 authored by Cong Wang, Nan Li, Wen-Jing Zhu, Jun-Fang Gong, Mao-Ping SongThe
first enantioselective Michael addition of 2-acetyl azaarenes
to β-CF3-β-(3-indolyl)nitroalkenes has
been successfully achieved in the presence of a Co(II)/(imidazoline-oxazoline)
complex as the catalyst. The reaction affords a series of CF3- and 3-indole-containing adducts featuring a trifluoromethylated
all-carbon quaternary stereocenter in good to excellent yields (up
to 99%) and enantioselectivities (up to 96% ee).
Furthermore, the functional groups in the adducts including CO,
NO2, and the azaarene provide a large variety of useful
transformations, leading to the formation of valuable intermediates
such as optically active secondary alcohol, pyrroline, ester, and
pyrrolidinone which all contain a 3-substituted indole and a trifluoromethylated
all-carbon quaternary stereocenter.