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Organocatalyst Efficiency in the α‐Aminoxylation and α‐Hydrazination of Carbonyl Derivatives in Aqueous Media or in a Ball‐Mill
Author(s) -
Veverková Eva,
Modrocká Viktória,
Šebesta Radovan
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601357
Subject(s) - chemistry , ball mill , aqueous solution , yield (engineering) , aqueous medium , pyrrolidine , organic chemistry , solvent , catalysis , nuclear chemistry , chemical engineering , engineering , metallurgy , materials science
Pyrrolidine‐derived organocatalysts have been tested in two types of α‐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 α‐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 α‐hydrazination reaction of 3‐phenylpropanal with dibenzyl azodicarboxylate by the ball‐milling technique.