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Green Asymmetric Synthesis : β ‐Amino Alcohol‐Catalyzed Direct Asymmetric Aldol Reactions in Aqueous Micelles
Author(s) -
Pinaka Afroditi,
Vougioukalakis Georgios C.,
Dimotikali Dimitra,
Yannakopoulou Elina,
Chankvetadze Bezhan,
Papadopoulos Kyriakos
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22120
Subject(s) - chemistry , aldol reaction , micelle , yield (engineering) , catalysis , organic chemistry , alcohol , aqueous solution , enantioselective synthesis , chirality (physics) , aqueous medium , pulmonary surfactant , amino acid , biochemistry , materials science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , metallurgy , quark
The ability of chiral β ‐amino alcohols to catalyze the direct asymmetric aldol reaction was evaluated for the first time in aqueous micellar media. A family of cheap and easily accessible β ‐amino alcohols, obtained in one step from naturally occurring amino acids, was shown to successfully catalyze the asymmetric aldol reaction between a series of ketones and aromatic aldehydes. These aldol reactions furnished the corresponding β ‐hydroxy ketones with up to 93% isolated yield and 89% ee. (S) ‐2‐phenylglycinol and Triton X‐100 proved to be the best organocatalyst and surfactant, respectively. Chirality 25:119–125, 2013 . © 2012 Wiley Periodicals, Inc.