ol500679w_si_001.cif (16.87 kB)
Trisubstituted 2‑Trifluoromethyl Pyrrolidines via Catalytic Asymmetric Michael Addition/Reductive Cyclization
dataset
posted on 2015-12-17, 01:56 authored by Michael
T. Corbett, Qihai Xu, Jeffrey S. JohnsonThe
stereoselective synthesis of trisubstituted 2-trifluoromethyl
pyrrolidines by asymmetric Michael addition/hydrogenative cyclization
is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones
to nitroolefins proceeds under mild reaction conditions and low catalyst
loadings to provide Michael adducts in high yield with excellent diastereo-
and enantioselectivity. Catalytic hydrogenation of the Michael adducts
stereoselectively generates 2-trifluoromethylated pyrrolidines
bearing three contiguous stereocenters. A stereospecific route to
epimeric 2-trifluoromethyl pyrrolidines from a common
intermediate is described.