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- Title
α-Alkyl-α-aryl (Trimethyltin) Nitriles: Versatile Nucleophilic Intermediates in Aldol-Like Reactions.
- Authors
Qin, Wenling; Long, Sha; Bongini, Alessandro; Panunzio, Mauro
- 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.
- Subjects
NITRILE synthesis; NUCLEOPHILIC reactions; TRIMETHYLTIN; ALDEHYDES; KETONES; KETENES
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 16, p3495
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500299