Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 8, Pages 1191-1195Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601357
Keywords
Asymmetric synthesis; Organocatalysis; Aldehydes; Aminoxylation; Hydrazination; Ball mill
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Funding
- Research & Development Operational Programme
- European Regional Development Fund [26240120025]
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Pyrrolidine-derived organocatalysts have been tested in two types of alpha-heterofunctionalization reactions in aqueous media or under solvent-free ball-milling conditions. The best results in terms of both activity and enantioselectivity were obtained with O-silylated 4-hydroxyproline derivatives in the alpha-aminoxylation reaction between n-butyraldehyde and nitrosobenzene (83 % yield in water, 86 % yield by ball milling and ee > 99 %). A very good yield (82 %) and excellent optical purity (ee > 99 %) were also achieved in the alpha-hydrazination reaction of 3-phenylpropanal with dibenzyl azodicarboxylate by the ball-milling technique.
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