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Castel Guelfo di Bologna, Italy

Qin W.,Institution Alma Materials Studiorum | Long S.,Institution Alma Materials Studiorum | Bongini A.,Institution Alma Materials Studiorum | Panunzio M.,CNR Institute for Organic Syntheses and Photoreactivity
European Journal of Organic Chemistry | Year: 2015

Abstract α-Alkyl-α-aryl (trimethyltin) nitriles react spontaneously with aldehydes and ketones in THF/toluene to give β-hydroxy nitriles with satisfactory to good yields and diastereoselectivity. No extra catalyst is required in this aldol-like reaction. A possible trimethyltin-substituted ketene imine intermediate is invoked as reactive species. DFT calculations offer good support for this hypothesis. α-Alkyl-α-aryl (trimethyltin) nitriles react spontaneously with aldehydes and ketones in THF/toluene to give β-hydroxy nitriles. A possible intermediate trimethyltin-ketene imine is invoked as reactive species. DFT calculations support this hypothesis. The new tin reagent may be considered an alternative option to the silylketene imines. Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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