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Enantioselective Organocatalytic Michael Additions of Oxyacetaldehydes to Nitroolefins
Author(s) -
Huťka Martin,
Poláčková Viera,
Marák Jozef,
Kaniansky Dušan,
Šebesta Radovan,
Toma Štefan
Publication year - 2010
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.201001032
Subject(s) - chemistry , enantioselective synthesis , michael reaction , yield (engineering) , enantiomeric excess , alkyl , enantiomer , organic chemistry , organocatalysis , mass spectrometry , catalysis , chromatography , materials science , metallurgy
Alkyl and aryloxyacetaldehydes add enantioselectively to various nitroalkenes. Addition products were isolated in good yield and high enantiomeric purity (up to 96 % ee ) but only mediocre syn / anti ratios were achieved. The course of the reaction was investigated by mass spectrometry and by DFT calculations.