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Organocatalyst Efficiency in the Michael Additions of Aldehydes to Nitroalkenes in Water and in a Ball‐Mill
Author(s) -
Veverková Eva,
Poláčková Viera,
Liptáková Lucia,
Kázmerová Eva,
Mečiarová Mária,
Toma Štefan,
Šebesta Radovan
Publication year - 2012
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200105
Subject(s) - ball mill , chemistry , pyrrolidine , aqueous solution , organocatalysis , catalysis , organic chemistry , enantioselective synthesis , michael reaction , chemical engineering , engineering
The enantioselective organocatalytic Michael addition in aqueous solution was compared with the reaction performed under solvent‐free ball‐milling conditions. A range of pyrrolidine‐derived organocatalysts were tested in the addition of aldehydes to nitroalkenes. Both procedures afforded good yields, diastereoselectivities, and enantioselectivities. The best catalyst in aqueous media was O ‐lauroyl‐ trans ‐4‐hydroxyproline, whilst the ball‐milling technique was most‐efficient with α,α‐diphenyl‐2‐pyrrolidinemethanol trimethylsilyl ether.