Publication | Closed Access
A New Asymmetric Synthesis of both Enantiomers of Coniine by 1,2‐Addition of RLi/YbCl<sub>3</sub> to Aldehyde SAMP Hydrazones
55
Citations
22
References
1993
Year
Diversity Oriented SynthesisEngineeringOrganoytterbium ReagentsNatural SciencesDiversity-oriented SynthesisAsymmetric SynthesisAldehyde Samp HydrazonesOrganic ChemistrySamp HydrazonesStereoselective SynthesisChemistryNew Asymmetric SynthesisPharmacologyAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
Abstract Both enantiomers of the hemlock alkaloid coniine 8 are prepared by asymmetric synthesis in 98% ee using only one enantiomer of the auxiliary. The key step of the synthesis consists in the 1,2‐addition of organoytterbium reagents to aldehyde SAMP hydrazones with virtually complete asymmetric induction, followed by N–N bond cleavage and cyclization.
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