Asymmetric hydrocarbofunctionalization of alkenes has emerged as an efficient strategy
for synthesizing optically active molecules through a carbon–carbon bond-forming process
from readily available alkenes and carboelectrophiles. Here, we present a summary
of our efforts to control the regio- and enantioselectivity of hydrocarbofunctionalizations
of electron-deficient alkenes with a nickel catalyst and a chiral bisoxazolidine ligand.
The reaction permits electron-reversed hydrocarbofunctionalizations of acrylamides
with excellent enantioselectivity. This operationally simple protocol permits the
asymmetric hydroalkylation, hydrobenzylation, or hydropropargylation of acrylamides.
This reaction is useful for preparing a wide range of α-branched chiral amides with
broad functional-group tolerance.
Key words
hydroalkylations - hydrobenzylations - hydropropargylations - hydrofunctionalizations
- asymmetric catalysis - cross-couplings
