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TMSCN/DBU-Mediated Facile Redox Transformation of α,β‑Unsaturated Aldehydes to Carboxylic Acid Derivatives

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journal contribution
posted on 07.02.2014, 00:00 by Hiromi Kaise, Jun Shimokawa, Tohru Fukuyama
Redox transformation of an α,β-unsaturated aldehyde to a carboxylic acid derivative by means of a combination of TMSCN and DBU was investigated. In addition to the wide use of the carboxylic acid derivatives provided by this reaction, temperature-dependent control of the kinetic or thermodynamic protonation pattern was found to selectively switch the stereochemistry of the acyl group in the product.