2012 journal article
An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones
Angewandte Chemie International Edition, 51(20), 4963–4967.
author keywords: asymmetric synthesis; homoenolates; homogeneous catalysis; Lewis acids; total synthesis
MeSH headings : Catalysis; Indoles / chemical synthesis; Indoles / chemistry; Lactones / chemical synthesis; Lactones / chemistry; Lewis Acids / chemistry; Methane / analogs & derivatives; Methane / chemistry; Molecular Structure; Spiro Compounds / chemical synthesis; Spiro Compounds / chemistry; Stereoisomerism
TL;DR:
A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed and has been used for the total synthesis of maremycin B.
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europepmc.org (repository)
Source: ORCID
Added: August 19, 2022
A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.