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Synlett 1999; 1999(10): 1630-1632
DOI: 10.1055/s-1999-2893
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Applications of the Baylis-Hillman Adducts in Organic Synthesis: A Facile Synthesis of [E]-α-Cyanocinnamyl Alcohols and [E]-α-Cyanocinnamic Aldehydes

Deevi Basavaiah* , Nagaswamy Kumaragurubaran, Kisari Padmaja
  • *School of Chemistry, University of Hyderabad, Hyderabad-500 046, India
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Publication Date:
31 December 1999 (online)

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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.

Baylis-Hillman reaction - [E]-α-cyanocinnamyl alcohols - [E]-α-cyanocinnamic aldehydes - isomerization - oxidation