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Applications of the Baylis-Hillman Adducts in Organic Synthesis: A Facile Synthesis of [<i>E</i>]-α-Cyanocinnamyl Alcohols and [<i>E</i>]-α-Cyanocinnamic Aldehydes
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1999
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Aqueous Sulfuric AcidEngineeringKnoevenagel Condensation ReactionNatural SciencesFacile SynthesisDiversity-oriented SynthesisBaylis-hillman AdductsOrganic ChemistryStereoselective SynthesisChemistryNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Aqueous sulfuric acid mediated transformation of the Baylis-Hillman adducts, i.e. 3-aryl-3-hydroxy-2-methylenepropanenitriles, into [E]-α-cyanocinnamyl alcohols and subsequent oxidation with PCC leading to the formation of stereochemically pure [E]-α-cyanocinnamic aldehydes, which represents an efficient alternative route to the Knoevenagel condensation reaction, is described.