Enantioselective N‑Heterocyclic Carbene Catalyzed
Synthesis of Functionalized Indenes
Posted on 2017-08-16 - 13:06
An 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.
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Zhang, Changhe; Lupton, David W. (2017). Enantioselective N‑Heterocyclic Carbene Catalyzed
Synthesis of Functionalized Indenes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01981
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