ol7b01981_si_001.pdf (28.43 MB)
Enantioselective N‑Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes
journal contribution
posted on 2017-08-16, 13:06 authored by Changhe Zhang, David W. LuptonAn enantioselective
NHC (N-heterocyclic carbene) catalyzed synthesis
of indenes from bifunctional α,β-unsaturated acyl fluorides
and TMS enol ethers has been discovered. The reaction has broad generality
(31 examples) and proceeds with high levels of enantioselectivity
(most >92:8 er). Mechanistically the reaction likely occurs via
a
Michael/β-lactonization/decarboxylation sequence. Derivatization
studies and limitations are discussed.