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Design of a Binaphthyl‐Based Axially Chiral Amino Acid as an Organocatalyst for Direct Asymmetric Aldol Reactions
Author(s) -
Kano Taichi,
Tokuda Osamu,
Takai Jun,
Maruoka Keiji
Publication year - 2006
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600077
Subject(s) - aldol reaction , adduct , chemistry , catalysis , yield (engineering) , acetone , proline , organic chemistry , organocatalysis , amino acid , enantioselective synthesis , materials science , biochemistry , metallurgy
A novel and robust binaphthyl‐based amino acid was designed and successfully applied to the direct asymmetric aldol reaction. In some cases, this catalyst leads to higher yields and selectivities than the well‐known proline catalyst. For instance, the direct asymmetric aldol reaction of acetone with 4‐nitrobenzaldehyde in the presence of the binaphthyl‐based amino acid catalyst proceeded smoothly to give the aldol adduct in 82 % yield with 95 % ee . This catalyst was also found to catalyze effectively the reactions of cyclic or unsymmetrical ketones to give the corresponding aldol adducts with excellent diastereo‐ and enantioselectivities.