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Unmodified Primary Amine Organocatalysts for Asymmetric Michael Reactions in Aqueous Media
Author(s) -
RogozińskaSzymczak Maria,
Mlynarski Jacek
Publication year - 2015
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.201500913
Subject(s) - chemistry , michael reaction , amine gas treating , organocatalysis , organic chemistry , aqueous solution , conjugate , primary (astronomy) , olefin fiber , nitro , aqueous medium , catalysis , solvent , nitroaldol reaction , enantioselective synthesis , mathematical analysis , physics , alkyl , mathematics , astronomy
The organocatalytic asymmetric Michael addition of aldehydes to a nitro olefin in aqueous organic solvents catalysed by a broad range of simple primary amines and amino alcohols is reported. In particular, the use of ( S , S )‐diphenylethylenediamine, which is the chiral backbone of various organocatalysts, gave addition products in good yields and with good to high enantioselectivities (45–96 % ee ). Remarkably high enantioselectivities were observed for the demanding conjugate addition of α,α‐disubstituted aldehydes to nitrostyrene (96–98 % ee ) in aqueous organic solvent mixtures.